CN110241148A - A kind of method of coproduction furfuryl alcohol and lactic acid - Google Patents
A kind of method of coproduction furfuryl alcohol and lactic acid Download PDFInfo
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Abstract
The invention discloses the methods of a kind of coproduction furfuryl alcohol and lactic acid: 1) pre-processing agriculture and forestry organic waste material to particle；2) it will be added in acid eutectic solvent after the drying of obtained particle, organic solvent be added, stirs and evenly mixs, reaction obtains the system containing furfural；3) system for obtaining step 2) is centrifuged to obtain residue, the organic phase containing furfural and eutectic solvent；4) by the obtained residual washing-out of centrifugation to neutrality；5) the neutral residue for obtaining step 4) uses cellulase degradation, and centrifugation obtains enzymolysis liquid；6) enzymolysis liquid that step 5) obtains and the organic phase containing furfural that step 3) obtains are mixed to form diphasic system；7) the system coproduction furfuryl alcohol and lactic acid obtained using whole-cell catalytic step 6).The present invention has the advantage that 1) acid flux material medium meets complete green, it is reusable；2) one-step method is reacted, and technique is simpler；3) reaction condition is mild, low energy consumption, low cost；4) furfuryl alcohol and lactic acid Poly-generation.
Description
Technical field
The present invention relates to the preparation methods of a kind of furfuryl alcohol and lactic acid coproduction, and in particular to a kind of " solvent engineering " invigoration effect
The method that biomass prepares furfuryl alcohol co-production of lactic acid.
Background technique
The problems such as with environmental pollution, energy shortages, climate warming it is increasingly serious, force the mankind look for it is novel can
The renewable sources of energy replace the disposable energy such as traditional coal, petroleum.China is large agricultural country, and agriculture and forestry organic waste material annual output is more than 6
Hundred million tons, but its utilization rate is lower, is mostly used in fuel wood or rots to discard, not only wastes resource, but also polluted atmosphere.Agricultural are useless
Gurry contains a large amount of carbon hydrogen element in composition, and has the advantages that stock number is big, low in cost, reproducible.Therefore, people
The visual field start to turn to lignocellulosic refining and obtain the energy and chemicals, furfural is a kind of as widely used chemicals
One of most promising mode, i.e., first convert platform chemicals furfural for lignocellulosic, be then converted to other chemicals and
Fuel.Traditional furfural industry is fully understanding furfural because energy consumption height, seriously polluted problem limit its development
On the basis of preparation principle, efficient, energy-saving and environment-friendly furfural production technology is established, develops furfural and other biological matter base product
Coproduction, for promoting the higher value application of renewable lignocellulose raw material to be of great significance.The DESs of choline chloride class has
The condition that the reaction medium of " completely green " should meet: it is environmental-friendly, there is reproducibility, it is cheap, it is nontoxic and
The preparation method is simple.These characteristics make it have certain advantage as ecological friendly reaction medium.
For furfural because it has active group, chemical property is active, further can obtain other high prices to its catalyzed conversion
Value platform chemicals (furfuryl alcohol, furancarboxylic acid, 2- methylfuran etc.) are to further synthesize valuable chemicals.Furfuryl alcohol is furfural
Hydrogenation products are that a very important intermediate can be used for synthesizing Vitamin C, lysine, lubricant and plasticizer etc..
Summary of the invention
Goal of the invention: the higher value application in order to realize agriculture and forestry organic waste material, the present invention provides a kind of coproduction furfuryl alcohol and creams
The method of acid.
Technical solution: a kind of method of coproduction furfuryl alcohol and lactic acid of the present invention, this method comprises the following steps:
1) agriculture and forestry organic waste material is pre-processed to particle；
2) it is added in acid eutectic solvent after the particle drying obtained step 1), organic solvent is added, stirs and evenly mixs,
80-200 DEG C of reaction 0.1-3h obtains the system containing furfural；
3) system for obtaining step 2) is centrifuged, and obtains residue, the organic phase containing furfural and eutectic solvent；
4) residual washing-out for obtaining step 3) centrifugation obtains neutral residue to neutrality；
5) the neutral residue for obtaining step 4) is digested using cellulase, and centrifugation obtains enzymolysis liquid；
6) enzymolysis liquid that step 5) obtains and the organic phase containing furfural that step 3) obtains are mixed to form diphasic system；
7) the system coproduction furfuryl alcohol and lactic acid obtained using whole-cell catalytic step 6).
In step 1), the agriculture and forestry organic waste material is corn stover, wheat stalk, rice husk, rice straw, corncob, sweet
Any one or the combination of several of them in bagasse or cotton seed hulls, preferably corncob；The pretreatment mode includes crushing, screening,
The partial size of the particle is 20~80 mesh (preferably 80 mesh).
In step 2), the acidity eutectic solvent includes sulfuric acid and eutectic solvent, and the eutectic solvent is choline
Villaumite type DESS.Preferably, the choline villaumite type DESSFor choline chloride/organic acid, preferably choline chloride/lactic acid, chlorination gallbladder
Alkali/malonic acid, choline chloride/malic acid, choline chloride/citric acid, choline chloride/oxalic acid or choline chloride/succinic acid, it is more excellent
Select choline chloride/oxalic acid.The acid choline villaumite type DESSPreparation method is as follows: the molar ratio of choline chloride and organic acid is
0.5-4:1 (preferably 1:1), sulfuric acid and choline villaumite type DESSThe mass ratio of middle choline chloride be 0.2-20:100,50-120 DEG C
To transparency liquid shape, the acidity eutectic solvent water content is 0-80wt% (preferably 0%) for stirring.The particle of the drying with
The mass ratio of eutectic solvent is 1-50:100 (preferably 5:100).
In step 2), it is preferable that 140 DEG C of reaction 30min obtain the system containing furfural.
In step 2), it is O-phthalic that the organic solvent, which is biocompatibility and the preferable organic solvent of extraction ability,
Any one or the combination of several of them in dioctyl phthalate, dibutyl phthalate, normal octane, n-hexane or toluene is (preferably adjacent
Dioctyl phthalate), the volume ratio of the organic solvent and eutectic solvent is 2-50:1.
In step 3), the centrifugal rotational speed be 5000-10000rpm, centrifugation time be 5-15min (preferably 5000rpm from
Heart 5min).
In step 4), using hot water (40-100 DEG C) filtering and washing residue to neutrality, the water content of neutral residue is 20-
90%.
In step 5), bone dry fiber element concentration is 5-50g/L (preferably 20g/L) in enzymatic hydrolysis system, and the cellulase is used
Amount is 5-50IU/g (preferably 40IU/g), based on bone dry fiber element；The enzymatic hydrolysis condition is as follows: pH be 4.5-6.0 (preferably
PH4.5), hydrolysis temperature is 40-55 DEG C (preferably 50 DEG C), and enzymolysis time is 12-72h (preferably 48h).Centrifugal condition after enzymatic hydrolysis
It is centrifuged 5-15min for 5000-10000rpm (preferably 5000rpm is centrifuged 5min).
In step 6), the volume ratio of the enzymolysis liquid and the organic phase containing furfural is 0.1-7.0:1 (preferably 1:1), described
The molar ratio of the furfural in glucose and organic phase in enzymolysis liquid is 1-5:1 (preferably 2.5:1).
In step 7), the full cell is lactic acid bacteria resting cell, and the dosage of the full cell is 0.5-4g (with weight in wet base
Meter) (preferably 1g)；The glucose and the mass ratio of full cell (in terms of weight in wet base) are 0.05-5:1, and the catalytic condition is as follows:
PH is 4.5-8.0, and reaction temperature is 30-55 DEG C, and the reaction time is 1-24h (preferably 45 DEG C reactions are for 24 hours).
The lactic acid bacteria is preferably bacillus alcalophilus CCTCC NO:M 2011468.Its classification of the bacillus alcalophilus
It is named as bacillus alcalophilus (Bacillus thermophilus), bacterial strain NL01, has been preserved in Chinese Typical Representative culture guarantor
Hiding center, preservation address are as follows: the Chinese Wuhan Wuhan University, postcode: 430072, deposit number are as follows: CCTCC NO:M
2011468, preservation date are as follows: on December 12nd, 2011, the bacterial strain are that inventor obtains in May, 2011 from soil screening
It arrives, is recorded in Chinese patent 201510882262X.
The utility model has the advantages that the present invention uses a kind of acid eutectic solvent, using cheap agriculture and forestry organic waste material as a raw material " step
Method " prepares important Biomass-based chemicals furfural.It is coupled with acid reaction medium with organic, in-situ synchronization is extracted furfural
It is mutually extracted into organic phase from reaction in time, realizes the reuse of acid reaction medium, improves furfural yield, simplification prepares chaff
The process route of aldehyde, reduces production cost, improves new approaches and new process for the preparation of furfural.For further furfural is turned
Valuable furfural derivatives are turned to, a kind of lactic acid bacteria Bacillus thermophilus of high concentration furfural tolerance is selected
NL01 is used for the Poly-generation of furfuryl alcohol and lactic acid, reacts mild, high production efficiency, the high-valued benefit for fully achieving agriculture and forestry organic waste material
With with huge prospects for commercial application.With the method or life reported in the literature for preparing furfural and furfuryl alcohol using biomass as raw material
Production. art is compared, and has the advantages that 1) acid flux material medium meets " green completely ", reusable；2) " one-step method " is anti-
It answers, technique is simpler, operates more convenient；3) reaction condition is mild, low energy consumption, low cost；4) furfuryl alcohol and lactic acid Poly-generation.
Detailed description of the invention
Fig. 1 is process flow chart of the invention.
Specific embodiment
Embodiment 1
Using small plant pulverizer respectively by corn stover, wheat stalk, rice husk, corncob, bagasse, cotton seed hulls
The particle of 80 mesh is screened after crushing.It weighs 1g over dry material to be placed in 20mL glassware, chlorination is added according to solid loadings 5%
In choline/oxalic acid (19g) eutectic solvent, wherein choline chloride and oxalic acid molar ratio are 1:1, while 1wt% sulfuric acid is added
(0.2g), 10mL dioctyl phthalate, 140 DEG C of reaction 30min.Reaction terminates centrifugation (5000rpm 5min) and obtains sample
It is analyzed, analyzes furfural yield such as table 1.
Furfural yield in 1 embodiment 1 of table
Embodiment 2
1g corncob over dry material core after weighing crushing and screening is placed in 20mL glassware, according to solid loadings 5%
It is separately added into choline chloride/lactic acid (molar ratio 1:1), choline chloride/malonic acid (molar ratio 1:1), choline chloride/apple
Acid (molar ratio 1:1), choline chloride/citric acid (molar ratio 1:1), choline chloride/oxalic acid (molar ratio 1:1), chlorination
In choline/succinic acid (molar ratio 1:1) (19g), while being separately added into 1wt% sulfuric acid (0.2g), 10mL phthalic acid two
Monooctyl ester, 140 DEG C of reaction 30min.Reaction terminates centrifugation (5000rpm 5min) acquisition sample and is analyzed, furfural yield such as table 2.
Furfural yield in 2 embodiment 2 of table
Embodiment 3
The residue that 2 choline chlorides of embodiment-oxalic acid system reacts is washed till neutrality, keeps water content 80% or so,
It is added in the conical flask of 50mL, enzymatic hydrolysis system 10mL, 20g/L (bone dry fiber element meter) processed corncob of DESs is residual
Slag is added the cellulase of 40IU/g (in terms of bone dry fiber element), supplies body using citrate buffer solution (pH4.5,100mM)
System.50 DEG C are subsequently placed in, digests 48h in the shaking table of 150rpm.Reaction terminates centrifugation (5000rpm5min) and obtains enzymolysis liquid, point
Analyse enzymolysis liquid ingredient such as table 3 after reaction.
3 enzymolysis liquid ingredient of table
Embodiment 4
Resting cell preparation method: Bacillus thermophilus NL01 uses kind first at 50 DEG C under 150rpm
Sub- culture medium preculture 12h.10% inoculum concentration is inoculated in fresh fermentation medium by volume, is placed in 50 DEG C,
Multiplying culture 12h in the shaking table of 150rpm.After Multiplying culture, thalline were collected by centrifugation (8000g, 3min, 4 DEG C), obtains
Thallus is washed twice with phosphate buffer (200mM, pH 7.0).
The seed culture based formulas is as follows: glucose 20g/L；Yeast Extract 2g/L；Dried Corn Steep Liquor Powder 2.5g/
L；NH4Cl 1g/L；MgSO40.2g/L；CaCO310g/L；pH 7.0-7.5.
The fermentative medium formula is as follows: glucose 40g/L；Yeast Extract 2.5g/L；Dried Corn Steep Liquor Powder
1.2g/L；(NH)2SO43；KH2PO40.22；MgSO4·7H2O 0.4；MnSO4·H2O 0.03；FeSO4·7H2O 0.03；
CaCO320；pH 7.0-7.5.
The organic phase structure of furfural is rich in the enzymolysis liquid and embodiment 2 that embodiment 3 is obtained in choline chloride-oxalic acid system
At diphasic system.10mL enzymolysis liquid (pH is adjusted to 7.0) is added in the conical flask of the tool plug of 50mL and 10mL contains having for furfural
Machine phase (molar ratio of furfural is 2.5:1 in glucose and organic phase), 50 DEG C, shake 1h under 100rpm after, it is (wet that 1.0g is added
Bacillus thermophilus NL01 cell is for being catalyzed Poly-generation furfuryl alcohol and lactic acid again).45 DEG C reaction for 24 hours, furfuryl alcohol and
Lactic acid content such as the following table 4.
4 furfuryl alcohol of table and lactic acid content
Comparative example 1
Resting cell preparation method: Bacillus thermophilus NL01 uses kind first at 50 DEG C under 150rpm
Sub- culture medium preculture 12h.It is inoculated in by 10% inoculum concentration in fresh fermentation medium, is placed in 50 DEG C, 150rpm's shakes
Multiplying culture 12h in bed.After Multiplying culture, thalline were collected by centrifugation (8000g, 3min, 4 DEG C), obtained thallus phosphoric acid
Salt buffer (200mM, pH 7.0) washes twice.
The enzymolysis liquid containing 14.73g/L glucose that 10mL embodiment 3 obtains is added in the conical flask of the tool plug of 50mL
(pH is adjusted to 7.0), while 1.0g (weight in wet base) Bacillus thermophilus NL01 cell is added for reacting.45 DEG C of reactions
For 24 hours, furfuryl alcohol and lactic acid content such as the following table 5.
5 furfuryl alcohol of table and lactic acid content
Comparative example 2
Resting cell preparation method: Bacillus thermophilus NL01 uses kind first at 50 DEG C under 150rpm
Sub- culture medium preculture 12h.It is inoculated in by 10% inoculum concentration in fresh fermentation medium, is placed in 50 DEG C, 150rpm's shakes
Multiplying culture 12h in bed.After Multiplying culture, thalline were collected by centrifugation (8000g, 3min, 4 DEG C), obtained thallus phosphoric acid
Salt buffer (200mM, pH 7.0) washes twice.
Choline chloride-oxalic acid system that 10mL embodiment 2 obtains is added in the conical flask of the tool plug of 50mL to contain
The organic phase of 3.16g/L furfural, while 1.0g (weight in wet base) Bacillus thermophilus NL01 cell is added for reacting.
45 DEG C are reacted for 24 hours, furfuryl alcohol and lactic acid content such as the following table 6.
6 furfuryl alcohol of table and lactic acid content
Claims (10)
1. a kind of method of coproduction furfuryl alcohol and lactic acid, which is characterized in that this method comprises the following steps:
1) agriculture and forestry organic waste material is pre-processed to particle；
2) it is added in acid eutectic solvent after the particle drying obtained step 1), organic solvent is added, stirs and evenly mixs, 80-
200 DEG C, reaction 0.1-3h obtains the system containing furfural；
3) system for obtaining step 2) is centrifuged, and obtains residue, the organic phase containing furfural and eutectic solvent；
4) residual washing-out for obtaining step 3) centrifugation obtains neutral residue to neutrality；
5) the neutral residue for obtaining step 4) is digested using cellulase, and centrifugation obtains enzymolysis liquid；
6) enzymolysis liquid that step 5) obtains and the organic phase containing furfural that step 3) obtains are mixed to form diphasic system；
7) the system coproduction furfuryl alcohol and lactic acid obtained using whole-cell catalytic step 6).
2. according to method as stated in claim 1, which is characterized in that agriculture and forestry organic waste material described in step 1) is corn stalk
Any one or the combination of several of them in stalk, wheat stalk, rice husk, rice straw, corncob, bagasse or cotton seed hulls；Institute
The partial size for stating particle is 20-80 mesh.
3. according to method as stated in claim 1, which is characterized in that acidity eutectic solvent described in step 2) includes sulphur
Acid and eutectic solvent, the eutectic solvent are choline villaumite type DESS。
4. according to the method described in claim 3, it is characterized in that, the sulfuric acid and choline villaumite type DESSMiddle choline chloride
Mass ratio is 0.2-20:100.
5. according to the method described in claim 3, it is characterized in that, the particle and eutectic solvent of drying described in step 2)
Mass ratio is 1-50:100.
6. the method according to claim 1, wherein organic solvent described in step 2) is that phthalic acid two is pungent
Any one or the combination of several of them in ester, dibutyl phthalate, normal octane, n-hexane or toluene, the organic solvent
Volume ratio with acid eutectic solvent is 2-50:1.
7. the method according to claim 1, wherein centrifugal rotational speed described in step 3) be 5000-10000rpm,
Centrifugation time is 5-15min.
8. the method according to claim 1, wherein bone dry fiber element concentration is 5- in enzymatic hydrolysis system in step 5)
50g/L, cellulase dosage are 5-50IU/g bone dry fiber element；The enzymatic hydrolysis condition is as follows: pH 4.5-6.0, hydrolysis temperature
It is 40-55 DEG C, enzymolysis time 12-72h.
9. the method according to claim 1, wherein in diphasic system described in step 6) enzymolysis liquid with contain furfural
The volume ratio of organic phase be 0.1-7.0:1, the molar ratio of furfural is 1-5:1 in glucose and organic phase in the enzymolysis liquid.
10. the method according to claim 1, wherein full cell described in step 7) be lactobacillus cell, it is described
The mass ratio of the glucose and full cell is 0.05-5:1, and full cell is in terms of weight in wet base；The catalytic condition is as follows: pH 4.5-
8.0, reaction temperature is 30-55 DEG C, reaction time 1-24h.
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| CN114480524A (en) * | 2021-12-16 | 2022-05-13 | 东莞理工学院 | Method for preparing furfuryl alcohol by catalyzing furfural |
| CN114736129A (en) * | 2022-04-06 | 2022-07-12 | 中国科学院成都有机化学有限公司 | Dicarboxylic acid-based eutectic solvent and preparation method and application thereof |
| NL2036566B1 (en) * | 2023-12-18 | 2024-08-09 | Inst Of Eco Environmental And Soil Sciences Guangdong Academy Of Sciences | Method for producing lactic acid by using waste straw |
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