CN109824632A - A method of 5 methyl furfural is prepared using biomass carbohydrates - Google Patents
A method of 5 methyl furfural is prepared using biomass carbohydrates Download PDFInfo
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- CN109824632A CN109824632A CN201910024962.3A CN201910024962A CN109824632A CN 109824632 A CN109824632 A CN 109824632A CN 201910024962 A CN201910024962 A CN 201910024962A CN 109824632 A CN109824632 A CN 109824632A
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- methyl furfural
- tungsten carbide
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Abstract
The present invention relates to a kind of methods for preparing 5 methyl furfural using biomass carbohydrates, include the following steps: successively to add biomass carbohydrates, tungsten carbide, distilled water, hydroiodic acid or iodine, organic solvent in reaction kettle, under the hydrogen atmosphere of 50~500psi, at a temperature of 90~200 DEG C, it is stirred to react 15~180min, ice-water bath is cooling, separates reaction solution, upper organic phase is separated, 5 methyl furfural is obtained after being further purified.5 methyl furfural of the present invention prepares raw material mainly from reproducible biomass carbohydrates；It using cheap and recyclable tungsten carbide catalyst, carries out under mild reaction conditions, reduces production cost, and of less demanding to production equipment, meet the principle of safety in production.
Description
Technical field
The invention belongs to biomass catalyzing method for transformation and compound synthesis method fields, and in particular to a kind of to utilize biology
The method that matter carbohydrate prepares 5 methyl furfural.
Background technique
Biomass resource is considered as the optimal selection for substituting fossil resource, and carrying out comprehensive effectively utilize to biomass is
One of the effective means of green chemistry chemical technology technology guarantee human kind sustainable development.5 methyl furfural is a kind of important fining
Product, are widely used in a kind of important composition of the industries such as medicine, pesticide, cosmetics or general flavorant, or even go back quilt
It is considered a kind of important anticancer drug；In addition, it is also used as recyclable fuel (high-quality diesel oil, 2,5- dimethyl furan
Mutter) important intermediate.Industrial 5 methyl furfural relies primarily on 5- methylfuran and expensive and high poison phosphoryl chloride phosphorus oxychloride or light
Solid/liquid/gas reactions prepare (J.Org.Chem.1957,22,1268-1269).Early in 1934, that is, there is document report 5 methyl furfural can
It reacts then to be handled with stannous chloride with hydrochloric acid from sucrose and be prepared, but whole process is up to for 24 hours, and last gained 5- first
Base furfural yield is no more than 7% (Org.Synth.1934,14,62).Books such as " the food additives handbook third editions " also refer to
5 methyl furfural can be obtained from various methylpentoses and acid together distillation, but not provide specific response parameter and reaction knot
Fruit.And Chinese patent CN201210288559.X report fructose based biomass mixed with acidic catalyst after with the side of fast pyrogenation
Method selectively obtains 5 methyl furfural, and pyrolysis time is no more than 1min, but the yield of 5 methyl furfural is also relatively low, up to
21%.In recent years, Chinese patent CN201410302966.0 discloses one kind in the presence of sodium iodide, with acid montmorillonite load
The catalyst of the noble metals such as ruthenium, palladium is catalyzed 5 hydroxymethyl furfural and prepares 5 methyl furfural (yield is through 130 DEG C of reaction 16h
90.9%).Elad Meller etc. is reported using 5- chloromethyl furfural or 5- bromomethyl furfural as substrate, is urged through active carbon-supported palladium
Agent catalyzed conversion 4h at 70 DEG C obtain 5 methyl furfural yield be about 99% (RSC Adv., 2016,6,103149-
103159).Above-mentioned 5 hydroxymethyl furfural, 5- chloromethyl furfural and 5- bromomethyl furfural can be from biomass saccharide compounds (such as
Fructose, glucose, sucrose, cellulose etc.) conversion obtains, and using them for substrate acquisition 5 methyl furfural, yield is equal for these researchs
It is higher, but the reaction time is long.And one kind reported in the literature is in benzene/water biphasic solvent, Pd/C or RuCl3、HI、H2In system
The method that one step conversion of biomass carbohydrate prepares 5 methyl furfural, the carbohydrate such as fructose act on through HI and generate 5- first
Base furfural and I2, and I2Again in catalyst, H2The lower reduction of effect generates the conversion that HI continues to participate in fructose, in the time less than 2h
The interior target product (Yang, W., Sen, A., 2011.ChemSusChem 4,349-352) for obtaining yield and being 68%.But
Free elemental iodine in-situ reducing is catalyzed into hydrogen iodide using expensive metal in reaction process, production cost is increased, if can make
It can effectively reduce the production cost of this method, with cheap metal displacement expensive metal to accelerate its industrialization.But in the reaction
In system, generally having cheap metal with hydrogenation efficiency, difficulty has preferable catalytic effect due to not being resistant to acid attack.Therefore it visits
Seeking acidproof non-noble metal hydrogenation catalyst is the weight that the carbohydrate conversions such as the fructose that hydroiodic acid participates in prepare 5 methyl furfural
Point and difficult point.
Summary of the invention
5 methyl furfural complex steps are prepared to make up existing biomass carbohydrates catalyzed conversion, are urged using noble metal
The deficiency of agent etc., the present invention provides a kind of method for preparing 5 methyl furfural using biomass carbohydrates, in hydrogen
Under acid iodide and the effect of cheap tungsten carbide catalyst, a step concerted catalysis conversion of biomass carbohydrate prepares 5 methyl furfural
Method:
The present invention has the advantages that simple, efficient, industrialization is at low cost, is easy to industrialization.So far, using your non-gold
Metal catalyst cooperates with one step of hydroiodic acid to convert to obtain the research of 5 methyl furfural document at home and abroad for biomass carbohydrates
In be not reported, which is of great significance.
The purpose of the present invention is achieved through the following technical solutions.
The present invention provides a kind of method for preparing 5 methyl furfural using biomass carbohydrates, includes the following steps:
Biomass carbohydrates, tungsten carbide, distilled water, hydroiodic acid or iodine, organic solvent are successively added with magnetic agitation
In the vial of son, under the hydrogen atmosphere of 50~500psi, at a temperature of 90~200 DEG C, it is stirred to react 15~180min, ice
Water-bath cooling separates reaction solution, separates upper organic phase, 5 methyl furfural is obtained after being further purified.
Further, the object of the tungsten carbide is mutually W2C、WC、WC2Deng one of or it is a variety of, wherein the preferably list of WC
Pure object phase.
Further, the tungsten carbide can be the non-loading type tungsten carbide catalyst of various different-shapes and structure；?
It can be and support in the support type tungsten carbide catalyst on different carriers.
Further, the tungsten carbide catalyst dosage (measuring by active component) is investment biomass carbohydrates
0.1~30wt%.
Further, the biomass carbohydrates are one of fructose, glucose, sucrose, inulin etc. or a variety of.
Further, the organic solvent is the common solvents such as benzene, toluene, tetrahydrofuran, ether, and dosage is distillation used
Appropriate saturated salt solution must be added when the solvent for selecting ether, tetrahydrofuran etc. to dissolve each other in 0.1-10 times of water volume.
Compared with prior art, the present invention the beneficial effect is that, the preparation of the biomass-based 5 methyl furfural of the present invention makes
With cheap tungsten carbide catalyst, production cost is largely reduced.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail.
It will be understood to those of skill in the art that the following example is merely to illustrate the present invention, and it should not be regarded as limiting this hair
Bright range.In the examples where no specific technique or condition is specified, described technology or conditions according to the literature in the art
Or it is carried out according to product description.Reagents or instruments used without specified manufacturer is that can be obtained by purchase
Conventional products.
Embodiment 1.
With magnetic stir bar 25ml quartz lining in, successively be added 0.1804g fructose, 30mg tungsten carbide (WC),
0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene, known quality n-decane, then medicine will be installed
The quartz lining opening of product is put in autoclave, kettle is closed, to continue to be flushed with hydrogen after the air in high-purity hydrogen replacement reaction kettle
Gas makes its internal pressure 300psi, is placed in reaction kettle in 130 DEG C of oil bath pan after detection is air tight and reacts 60min, sufficiently
After cooling, kettle is opened in exhaust, and upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, and testing result shows 5 methyl furfural
Molar yield be 61%.
Embodiment 2.
With magnetic stir bar 25ml quartz lining in, successively be added 0.1803g fructose, 30mg tungsten carbide (WC),
0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 8ml toluene, known quality n-decane, then medicine will be installed
The quartz lining opening of product is put in autoclave, kettle is closed, to continue to be flushed with hydrogen after the air in high-purity hydrogen replacement reaction kettle
Gas makes its internal pressure 200psi, is placed in reaction kettle in 130 DEG C of oil bath pan after detection is air tight and reacts 60min, sufficiently
After cooling, kettle is opened in exhaust, and upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, and testing result shows 5 methyl furfural
Molar yield be 63%.
Embodiment 3.
With magnetic stir bar 25ml quartz lining in, successively be added 0.1804g fructose, 40mg tungsten carbide (WC),
0.5ml mass fraction be 55~58% hydroiodic acids, 1.5ml distilled water, 5ml toluene, known quality n-decane, then medicine will be installed
The quartz lining opening of product is put in autoclave, kettle is closed, to continue to be flushed with hydrogen after the air in high-purity hydrogen replacement reaction kettle
Gas makes its internal pressure 300psi, is placed in reaction kettle in 130 DEG C of oil bath pan after detection is air tight and reacts 60min, sufficiently
After cooling, kettle is opened in exhaust, and upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, and testing result shows 5 methyl furfural
Molar yield be 58%.
Embodiment 4.
With magnetic stir bar 25ml quartz lining in, successively be added 0.1804g fructose, 30mg tungsten carbide (WC),
0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene, known quality n-decane, then medicine will be installed
The quartz lining opening of product is put in autoclave, kettle is closed, to continue to be flushed with hydrogen after the air in high-purity hydrogen replacement reaction kettle
Gas makes its internal pressure 200psi, is placed in reaction kettle in 130 DEG C of oil bath pan after detection is air tight and reacts 60min, sufficiently
After cooling, kettle is opened in exhaust, and upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, and testing result shows 5 methyl furfural
Molar yield be 62%.
Embodiment 5.
With magnetic stir bar 25ml quartz lining in, successively be added 0.1803g fructose, 30mg tungsten carbide (WC),
0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene, known quality n-decane, then medicine will be installed
The quartz lining opening of product is put in autoclave, kettle is closed, to continue to be flushed with hydrogen after the air in high-purity hydrogen replacement reaction kettle
Gas makes its internal pressure 200psi, is placed in reaction kettle in 130 DEG C of oil bath pan after detection is air tight and reacts 45min, sufficiently
After cooling, kettle is opened in exhaust, and upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, and testing result shows 5 methyl furfural
Molar yield be 58%.
Embodiment 6.
In the 25ml quartz lining with magnetic stir bar, 0.1797g glucose, 30mg tungsten carbide is successively added
(WC), 0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene, known quality n-decane, then will
The quartz lining opening for installing drug is put in autoclave, closes kettle, subsequent with the air in high-purity hydrogen replacement reaction kettle
It is continuous to be flushed with hydrogen gas, make its internal pressure 200psi, reaction kettle is placed in 160 DEG C of oil bath pan and is reacted after detection is air tight
60min, after being fully cooled, kettle is opened in exhaust, takes upper toluene mutually through diluting laggard promoting the circulation of qi analysis of hplc, testing result is shown
The mass yield of 5 methyl furfural is 20%.
Embodiment 7.
With magnetic stir bar 25ml quartz lining in, successively be added 0.1802g sucrose, 30mg tungsten carbide (WC),
0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene, known quality n-decane, then medicine will be installed
The quartz lining opening of product is put in autoclave, kettle is closed, to continue to be flushed with hydrogen after the air in high-purity hydrogen replacement reaction kettle
Gas makes its internal pressure 200psi, is placed in reaction kettle in 160 DEG C of oil bath pan after detection is air tight and reacts 60min, sufficiently
After cooling, kettle is opened in exhaust, and upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, and testing result shows 5 methyl furfural
Mass yield be 22%.
Embodiment 8.
With magnetic stir bar 25ml quartz lining in, successively be added 0.1802g inulin, 30mg tungsten carbide (WC),
0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene, known quality n-decane, then medicine will be installed
The quartz lining opening of product is put in autoclave, kettle is closed, to continue to be flushed with hydrogen after the air in high-purity hydrogen replacement reaction kettle
Gas makes its internal pressure 200psi, is placed in reaction kettle in 160 DEG C of oil bath pan after detection is air tight and reacts 60min, sufficiently
After cooling, kettle is opened in exhaust, and upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, and testing result shows 5 methyl furfural
Mass yield be 30%.
Embodiment 9.
In the 25ml quartz lining with magnetic stir bar, 0.18g fructose is successively added, (WC is used 12.3mg tungsten carbide
Amount is equivalent to the 6.3eq% of fructose additional amount), 0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml first
The n-decane of benzene, known quality, then the quartz lining opening for installing drug is put in autoclave, kettle is closed, with High Purity Hydrogen
Continue to be flushed with hydrogen gas after air in gas replacement reaction kettle, makes its internal pressure 200psi, set reaction kettle after detection is air tight
60min is reacted in 130 DEG C of oil bath pan, after being fully cooled, kettle is opened in exhaust, takes upper toluene mutually through diluting laggard promoting the circulation of qi phase
Chromatography, testing result show that the molar yield of 5 methyl furfural is 54%.
Comparative example 1.
In the 25ml quartz lining with magnetic stir bar, 0.18g fructose, palladium charcoal (the wherein quality of palladium is successively added
Score is 5%, and dosage is equivalent to the 6.3eq% of fructose additional amount), 0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml
Distilled water, 5ml toluene, known quality n-decane, then the quartz lining opening for installing drug is put in autoclave, is closed
Kettle makes its internal pressure 200psi, after detection is air tight to continue to be flushed with hydrogen gas after the air in high-purity hydrogen replacement reaction kettle
Reaction kettle is placed in 130 DEG C of oil bath pan and reacts 60min, after being fully cooled, exhaust opens kettle, takes upper toluene mutually through diluting
Laggard promoting the circulation of qi analysis of hplc, testing result show that the molar yield of 5 methyl furfural is 54%.
Comparative example 2.
In the 25ml quartz lining with magnetic stir bar, 0.18g fructose, molybdenum carbide (MoC, dosage phase is successively added
When in the 6.3eq% of fructose additional amount), 0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene,
Know the n-decane of quality, then the quartz lining opening for installing drug is put in autoclave, closes kettle, replaced with high-purity hydrogen
Continue to be flushed with hydrogen gas after air in reaction kettle, makes its internal pressure 200psi, reaction kettle is placed in 130 DEG C after detection is air tight
Oil bath pan in react 60min, after being fully cooled, kettle is opened in exhaust, and upper toluene is taken mutually to carry out gas-chromatography point after diluting
Analysis, testing result show that the molar yield of 5 methyl furfural is 44%.
Comparative example 3.
In the 25ml quartz lining with magnetic stir bar, 0.18g fructose, catalyst of phosphatizing nickel (dosage is successively added
Be equivalent to the 6.3eq% of fructose additional amount), 0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene,
The n-decane of known quality, then the quartz lining opening for installing drug is put in autoclave, kettle is closed, is set with high-purity hydrogen
Continue to be flushed with hydrogen gas after changing the air in reaction kettle, makes its internal pressure 200psi, reaction kettle is placed in 130 after detection is air tight
DEG C oil bath pan in react 60min, after being fully cooled, kettle is opened in exhaust, and upper toluene is taken mutually to carry out gas-chromatography point after diluting
Analysis, testing result show that the molar yield of 5 methyl furfural is 47%.
Comparative example 4.
In the 25m1 quartz lining with magnetic stir bar, 0.18g fructose, phosphatization iron catalyst (dosage is successively added
Be equivalent to the 6.3eq% of fructose additional amount), 0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene,
The n-decane of known quality, then the quartz lining opening for installing drug is put in autoclave, kettle is closed, is set with high-purity hydrogen
Continue to be flushed with hydrogen gas after changing the air in reaction kettle, makes its internal pressure 200psi, reaction kettle is placed in 130 after detection is air tight
DEG C oil bath pan in react 60min, after being fully cooled, kettle is opened in exhaust, and upper toluene is taken mutually to carry out gas-chromatography point after diluting
Analysis, testing result show that the molar yield of 5 methyl furfural is 41%.
Comparative example 5.
In the 25ml quartz lining with magnetic stir bar, 0.18g fructose, phosphatization Co catalysts (dosage is successively added
Be equivalent to the 6.3eq% of fructose additional amount), 0.4ml mass fraction be 55~58% hydroiodic acids, 1.6ml distilled water, 5ml toluene,
The n-decane of known quality, then the quartz lining opening for installing drug is put in autoclave, kettle is closed, is set with high-purity hydrogen
Continue to be flushed with hydrogen gas after changing the air in reaction kettle, makes its internal pressure 200psi, reaction kettle is placed in 130 after detection is air tight
DEG C oil bath pan in react 60min, after being fully cooled, kettle is opened in exhaust, and upper toluene is taken mutually to carry out gas-chromatography point after diluting
Analysis, testing result show that the molar yield of 5 methyl furfural is 48%.
Comparative example 6.
In the 25m1 quartz lining with magnetic stir bar, 0.18g fructose is successively added, 0.4ml mass fraction is 55
~58% hydroiodic acid, 1.6ml distilled water, 5ml toluene, known quality n-decane, then will install drug quartz lining it is open
It is put in autoclave, closing kettle to continue to be flushed with hydrogen gas after the air in high-purity hydrogen replacement reaction kettle makes its internal pressure
Reaction kettle is placed in 130 DEG C of oil bath pan after detection is air tight and reacts 60min by 200psi, and after being fully cooled, kettle is opened in exhaust,
Upper toluene is taken mutually to be diluted laggard promoting the circulation of qi analysis of hplc, testing result shows that the molar yield of 5 methyl furfural is 43%.
The following table 1 lists tungsten carbide compared with palladium charcoal and other common non-noble metal catalytic activity.From embodiment 9 and right
Ratio 1 is as can be seen that under the same conditions, cheap tungsten carbide is suitable with expensive palladium carbon catalyst activity；And it can from ratio 2~6
To find out, the common non-noble metal hydrogenation catalyst that often replacement palladium charcoal uses in many occasions is in the system to 5 methyl furfural
Generation influence it is unobvious, illustrate not be commonly used for replace platinum-group noble metals cheap metal catalyst all can preferably be used for
The 5 methyl furfural is prepared in reaction system.
1 tungsten carbide of table is compared with palladium charcoal and other common non-noble metal catalytic activity
| Catalyst type | Fructose dosage | Catalyst is equivalent to the dosage of fructose | 5 methyl furfural yield | |
| Embodiment 9 | Tungsten carbide (wC) | 0.18g | ≈ 6.3eq% | 54% |
| Comparative example 1 | Palladium charcoal | 0.18g | ≈ 6.3eq% | 54% |
| Comparative example 2 | Molybdenum carbide (MoC) | 0.18g | ≈ 6.3eq% | 44% |
| Comparative example 3 | Catalyst of phosphatizing nickel | 0.18g | ≈ 6.3eq% | 47% |
| Comparative example 4 | Phosphatization iron catalyst | 0.18g | ≈ 6.3eq% | 41% |
| Comparative example 5 | Phosphatization Co catalysts | 0.18g | ≈ 6.3eq% | 48% |
| Comparative example 6 | Catalyst is not added | 0.18g | 0% | 43% |
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention is by the attached claims and its waits
Effect object defines.
Claims (6)
1. a kind of method for preparing 5 methyl furfural using biomass carbohydrates, which comprises the steps of: will
Biomass carbohydrates, tungsten carbide, distilled water, hydroiodic acid or iodine, organic solvent are successively added in reaction kettle, 50~
The hydrogen atmosphere of 500psi at a temperature of 90~200 DEG C, is stirred to react 15~180min, and ice-water bath is cooling, separates reaction solution, point
It is purified to obtain 5 methyl furfural from upper organic phase.
2. a kind of method for preparing 5 methyl furfural using biomass carbohydrates according to claim 1, feature
It is, the object of the tungsten carbide is mutually the simple object phase of WC.
3. a kind of method for preparing 5 methyl furfural using biomass carbohydrates according to claim 1 or 2, special
Sign is that the tungsten carbide is the non-loading type tungsten carbide catalyst of different-shape and structure, or to support on different carriers
Support type tungsten carbide catalyst.
4. a kind of method for preparing 5 methyl furfural using biomass carbohydrates according to claim 1, feature
It is, the dosage (measuring by active component) of the tungsten carbide is 0.1~30wt% of investment biomass carbohydrates.
5. a kind of method for preparing 5 methyl furfural using biomass carbohydrates according to claim 1, feature
It is, the biomass carbohydrates are one of fructose, glucose, sucrose, inulin, cellulose or a variety of.
6. a kind of method for preparing 5 methyl furfural using biomass carbohydrates according to claim 1, feature
It is, the organic solvent is benzene, toluene, tetrahydrofuran or ether, and dosage is 0.1-10 times of distilled water volume used.
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| CN112007676A (en) * | 2020-09-11 | 2020-12-01 | 华中科技大学 | Super-hydrophobic high-dispersion supported tungsten carbide catalyst and preparation method and application thereof |
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| US20110282079A1 (en) * | 2009-06-05 | 2011-11-17 | The Penn State Research Foundation | One-step catalytic conversion of biomass-derived carbohydrates to liquid fuels |
| CN108250165A (en) * | 2018-01-10 | 2018-07-06 | 南昌大学 | A kind of method for preparing N- (5- methyl furfuryl group) aniline and derivative using biomass carbohydrates |
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| US20110282079A1 (en) * | 2009-06-05 | 2011-11-17 | The Penn State Research Foundation | One-step catalytic conversion of biomass-derived carbohydrates to liquid fuels |
| CN108250165A (en) * | 2018-01-10 | 2018-07-06 | 南昌大学 | A kind of method for preparing N- (5- methyl furfuryl group) aniline and derivative using biomass carbohydrates |
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| CN112007676A (en) * | 2020-09-11 | 2020-12-01 | 华中科技大学 | Super-hydrophobic high-dispersion supported tungsten carbide catalyst and preparation method and application thereof |
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