CN105498801A - Preparation method of sulfated carbonized corn cob catalyst and method for preparing furfural from xylose in presence of catalyst - Google Patents
Preparation method of sulfated carbonized corn cob catalyst and method for preparing furfural from xylose in presence of catalyst Download PDFInfo
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- CN105498801A CN105498801A CN201511025599.5A CN201511025599A CN105498801A CN 105498801 A CN105498801 A CN 105498801A CN 201511025599 A CN201511025599 A CN 201511025599A CN 105498801 A CN105498801 A CN 105498801A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
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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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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the technical field of preparation of biomass-based chemicals and discloses a preparation method of a sulfated carbonized corn cob catalyst and a method for preparing furfural from xylose in presence of the catalyst. The method comprises the steps of heating absolutely dry corn cob powder in a carbonization furnace to 400-500 DEG C in an atmosphere of nitrogen gas and carbonizing for 4-6h to obtain carbonized corn cob; adding the carbonized corn cob and concentrated sulfuric acid into a reactor and reacting at 145-155 DEG C for 14-16h; washing and drying the reaction product to obtain the sulfated carbonized corn cob catalyst; placing xylose-containing hydrolysis liquid, the sulfated carbonized corn cob catalyst and dichloromethane in the reactor and reacting at 160-180 DEG C for 1.5-2.5h, and performing separation and purification on the reaction product to obtain furfural. The sulfated carbonized corn cob catalyst has high catalytic efficiency, is low in cost, and can remarkably improve the yield of furfural and reduce the production cost of furfural when used for preparing furfural from xylose.
Description
Technical field
The invention belongs to living beings chemicals preparing technical field, be specifically related to a kind of sulfonated preparation of charing corncob catalyst and the method for catalysis Furfural Production from Xylose thereof.
Background technology
Along with the exhaustion day by day of non-renewable primary energy-fossil energy, countries in the world start the saving paying attention to non-renewable energy one after another, and accelerate the research and development to the renewable sources of energy-biomass energy.Wood fiber biomass is because of its environmental friendliness, and the advantage such as rich reserves, cheapness, industrial development, problem of environmental pollution will play an important role.
Furfural, also known as furtural, being one of furans system important derivatives, being dewatered and obtain by agricultural byproducts gained poly-pentose after high temperature acidolysis, is a kind of important Organic Chemicals and chemical solvent of being widely used in the industries such as petroleum industry, Chemical Manufacture, medicine, food and synthesis macromolecule.Produce furfural raw material type a lot, be mainly rich in pentosan agricultural products, as corncob, wood chip, bagasse, straw etc.
Furfural is hydrolyzed into pentose in acid condition by poly-pentose, then formed by dehydration of pentoses cyclisation.Whether furfural production technology is undertaken being divided into method by single-stage and two-stage method by a step according to hydrolysis and dehydration.According to the difference of catalyst, diluted acid method, inorganic salts catalysis method, solid acid catalysis method etc. can be divided into.In recent years, utilize solid acid catalysis to transform agricultural biomass and prepare the extensive concern that the energy and high valuable chemicals technique are more and more subject to scientific worker.Its feature of solid acid catalysis is that catalytic efficiency is high, energy ezpenditure is low, catalyst less on equipment impact can recycle.Utilize solid acid catalyst to replace conventional mineral acid catalyst greatly can overcome severe reaction conditions, environmental pollution, the shortcomings such as equipment corrosion, possess skills feasibility upper and economically.Existing solid acid mainly comprises the brand-new materials such as metal oxide, resinous matter and Graphene, this class solid acid catalysis effect is all very remarkable, but do not possess economic serviceability, this is the main bottleneck of restriction solid acid industrially use of large-scale production.Catalysis Furfural Production from Xylose can be divided into single-phase catalysis and heterogeneous catalysis according to the difference of reaction system, and wherein introduction organic reagent and aqueous phase form the catalyst system and catalyzing effect of two-phase very significantly, have now been widely used at furfural Catalysis experiments probe process.In aqueous phase, wood sugar dehydration to be transformed into after furfural rapidly by organic extractant phase, so just achieves being separated of furfural and wood sugar, avoids wood sugar and furfural resinification at high temperature and generates humus and reduce furfural productive rate.
Summary of the invention
In order to solve the shortcoming and defect part of above prior art, primary and foremost purpose of the present invention is the preparation method providing a kind of sulfonated charing corncob catalyst.
Another object of the present invention is to provide a kind of sulfonated charing corncob catalyst prepared by said method.
Of the present inventionly be to provide a kind of method adopting above-mentioned sulfonated charing corncob catalyst Furfural Production from Xylose in an object.
The object of the invention is achieved through the following technical solutions:
A preparation method for sulfonated charing corncob catalyst, comprises following preparation process:
Over dry corncob powder is placed in retort, is warming up to 400 ~ 500 DEG C of charing 4 ~ 6h under nitrogen atmosphere, obtains carbonizing corncob; Then join in reactor by charing corncob and the concentrated sulfuric acid, at 145 ~ 155 DEG C of temperature, react 14 ~ 16h, product, through washing, oven dry, obtains sulfonated charing corncob catalyst.
Preferably, the order number of described over dry corncob is 80 ~ 120 orders.
Preferably, described nitrogen atmosphere refers to that maintaining nitrogen flux is 40 ~ 60mL/min.
Preferably, the w/v of described charing corncob and the concentrated sulfuric acid is 1:30g/mL.
Preferably, described washing refers to washing to product in neutral; The time of described oven dry is 10 ~ 14h.
A kind of sulfonated charing corncob catalyst, is prepared by said method.
Adopt a method for above-mentioned sulfonated charing corncob catalyst Furfural Production from Xylose, comprise following preparation process:
Corncob and oxalic acid are carried out ball milling, and then adding water is placed in microwave reaction kettle and reacts, and obtains the hydrolyzate containing wood sugar; Then be placed in reactor by containing the hydrolyzate of wood sugar, sulfonated charing corncob catalyst and carrene, at 160 ~ 180 DEG C of temperature, react 1.5 ~ 2.5h, product, through separation and purification, obtains furfural.
Preferably, described is 5% ~ 7% containing the mass percentage of wood sugar in the hydrolyzate of wood sugar.
Preferably, the described hydrolyzate containing wood sugar: sulfonated charing corncob catalyst: the ratio of the addition of carrene is (2 ~ 4) mL:(0.02 ~ 0.04) g:(4 ~ 8) mL.
Preparation method of the present invention and the product tool obtained have the following advantages and beneficial effect:
(1) the sulfonated charing corncob catalyst prepared of the present invention, has high, selective good, the renewable and reusable edible of catalytic efficiency, acid strength is large, and the advantage such as cost of manufacture is cheap;
(2) the sulfonated charing corncob catalyst that prepared by the present invention is rich in wood sugar in xylose hydrolysis fluid in catalysis and generates in the process of furfural, reaction condition is gentle, easy controlled operation, be easy to realize industrialization, course of reaction adding without mineral acid, avoid equipment corrosion, there is environment friendly, energy-saving and emission-reduction object can be reached, reduce furfural production cost.
Accompanying drawing explanation
Fig. 1 is a kind of sulfonated preparation of charing corncob catalyst of the embodiment of the present invention 1 ~ 3 and the process chart of the method for catalysis Furfural Production from Xylose thereof.
Detailed description of the invention
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
A kind of sulfonated preparation of charing corncob catalyst of the present embodiment and the method for catalysis Furfural Production from Xylose thereof, its process chart as shown in Figure 1.Concrete preparation process is as follows:
(1) preparation charing corncob: add 5g over dry corncob (80 order) and be placed in vacuum tube furnace and airtight good in ceramic crucible, logical nitrogen, nitrogen flux is 40mL/min, and carbonization temperature is 400 DEG C, and carbonization time is 4h;
(2) sulfonated charing corncob catalyst is prepared: in tetrafluoroethene retort, add the charing corncob and the 24mL concentrated sulfuric acid that obtain in 0.8g step (1), be placed in baking oven and react 14h at 145 DEG C, after reaction terminates, cooling, filter, solids wash is 6.8 to pH, dry 10h in baking oven;
(3) preparation is containing the hydrolyzate of wood sugar: corncob and oxalic acid are carried out ball milling, then adds water to be placed in microwave reaction kettle and to react, and obtains the hydrolyzate containing wood sugar; Xylose Content in hydrolyzate is 5% (wt);
(4) catalyst Furfural Production from Xylose: add 2mL step (3) gained containing the sulfonated charing corncob catalyst obtained in the hydrolyzate of wood sugar, 0.02g step (2) and 4mL carrene in tetrafluoroethene retort, be placed in baking oven and react 1.5h at 160 DEG C, after reaction terminates, cooling, is separated the organic phase obtaining being rich in furfural and the aqueous phase containing a small amount of furfural with separatory funnel.
Furfural content in wood sugar in aqueous phase and furfural and organic phase measures by high performance liquid chromatograph (HPLC).
Furfural yield=(the furfural molal quantity in the furfural molal quantity+organic phase in the aqueous phase that HPLC records)/add reaction hydrolyzate wood sugar molal quantity × 100%;
Xylose rate=(originally in hydrolyzate in wood sugar quality-residue aqueous phase wood sugar quality)/originally wood sugar quality × 100%;
Through calculating, the furfural yield of the present embodiment is 78%, and wherein aqueous phase furfural yield is 1.0%, and xylose rate is 96%.
Embodiment 2
A kind of sulfonated preparation of charing corncob catalyst of the present embodiment and the method for catalysis Furfural Production from Xylose thereof, its process chart as shown in Figure 1.Concrete preparation process is as follows:
(1) preparation charing corncob: add 6g over dry corncob (100 order) and be placed in vacuum tube furnace and airtight good in ceramic crucible, logical nitrogen, nitrogen flux is 50mL/min, and carbonization temperature is 450 DEG C, and carbonization time is 5h;
(2) sulfonated charing corncob catalyst is prepared: in tetrafluoroethene retort, add the charing corncob and the 30mL concentrated sulfuric acid that obtain in 1.0g step (1), be placed in baking oven and react 15h at 150 DEG C, after reaction terminates, cooling, filter, solids wash is 7.0 to pH, dry 12h in baking oven;
(3) preparation is containing the hydrolyzate of wood sugar: corncob and oxalic acid are carried out ball milling, then adds water to be placed in microwave reaction kettle and to react, and obtains the hydrolyzate containing wood sugar; Xylose Content in hydrolyzate is 6% (wt);
(4) catalyst Furfural Production from Xylose: add 3mL step (3) gained containing the sulfonated charing corncob catalyst obtained in the hydrolyzate of wood sugar, 0.03g step (2) and 6mL carrene in tetrafluoroethene retort, be placed in baking oven and react 2h at 170 DEG C, after reaction terminates, cooling, is separated the organic phase obtaining being rich in furfural and the aqueous phase containing a small amount of furfural with separatory funnel.
Furfural content in wood sugar in aqueous phase and furfural and organic phase measures by high performance liquid chromatograph (HPLC).
Furfural yield=(the furfural molal quantity in the furfural molal quantity+organic phase in the aqueous phase that HPLC records)/add reaction hydrolyzate wood sugar molal quantity × 100%;
Xylose rate=(originally in hydrolyzate in wood sugar quality-residue aqueous phase wood sugar quality)/originally wood sugar quality × 100%;
Through calculating, the furfural yield of the present embodiment is 80%, and wherein aqueous phase furfural yield is 1.2%, and xylose rate is 97%.
Embodiment 3
A kind of sulfonated preparation of charing corncob catalyst of the present embodiment and the method for catalysis Furfural Production from Xylose thereof, its process chart as shown in Figure 1.Concrete preparation process is as follows:
(1) preparation charing corncob: add 7g over dry corncob (120 order) and be placed in vacuum tube furnace and airtight good in ceramic crucible, logical nitrogen, nitrogen flux is 60mL/min, and carbonization temperature is 500 DEG C, and carbonization time is 6h;
(2) sulfonated charing corncob catalyst is prepared: in tetrafluoroethene retort, add the charing corncob and the 36mL concentrated sulfuric acid that obtain in 1.2g step (1), be placed in baking oven and react 16h at 155 DEG C, after reaction terminates, cooling, filter, solids wash is 7.2 to pH, dry 14h in baking oven;
(3) preparation is containing the hydrolyzate of wood sugar: corncob and oxalic acid are carried out ball milling, then adds water to be placed in microwave reaction kettle and to react, and obtains the hydrolyzate containing wood sugar; Xylose Content in hydrolyzate is 7% (wt);
(4) catalyst Furfural Production from Xylose: add 4mL step (3) gained containing the sulfonated charing corncob catalyst obtained in the hydrolyzate of wood sugar, 0.04g step (2) and 8mL carrene in tetrafluoroethene retort, be placed in baking oven and react 2.5h at 180 DEG C, after reaction terminates, cooling, is separated the organic phase obtaining being rich in furfural and the aqueous phase containing a small amount of furfural with separatory funnel.
Furfural content in wood sugar in aqueous phase and furfural and organic phase measures by high performance liquid chromatograph (HPLC).
Furfural yield=(the furfural molal quantity in the furfural molal quantity+organic phase in the aqueous phase that HPLC records)/add reaction hydrolyzate wood sugar molal quantity × 100%;
Xylose rate=(originally in hydrolyzate in wood sugar quality-residue aqueous phase wood sugar quality)/originally wood sugar quality × 100%;
Through calculating, the furfural yield of the present embodiment is 82%, and wherein aqueous phase furfural yield is 1.4%, and xylose rate is 98%.
Above-described embodiment is the present invention's preferably embodiment; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from Spirit Essence of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (9)
1. a preparation method for sulfonated charing corncob catalyst, is characterized in that comprising following preparation process:
Over dry corncob powder is placed in retort, is warming up to 400 ~ 500 DEG C of charing 4 ~ 6h under nitrogen atmosphere, obtains carbonizing corncob; Then join in reactor by charing corncob and the concentrated sulfuric acid, at 145 ~ 155 DEG C of temperature, react 14 ~ 16h, product, through washing, oven dry, obtains sulfonated charing corncob catalyst.
2. the preparation method of a kind of sulfonated charing corncob catalyst according to claim 1, is characterized in that: the order number of described over dry corncob is 80 ~ 120 orders.
3. the preparation method of a kind of sulfonated charing corncob catalyst according to claim 1, is characterized in that: described nitrogen atmosphere refers to that maintaining nitrogen flux is 40 ~ 60mL/min.
4. the preparation method of a kind of sulfonated charing corncob catalyst according to claim 1, is characterized in that: the w/v of described charing corncob and the concentrated sulfuric acid is 1:30g/mL.
5. the preparation method of a kind of sulfonated charing corncob catalyst according to claim 1, is characterized in that: described washing refers to washing to product in neutral; The time of described oven dry is 10 ~ 14h.
6. a sulfonated charing corncob catalyst, be is characterized in that: prepared by the method described in any one of Claims 1 to 5.
7. adopt a method for sulfonated charing corncob catalyst Furfural Production from Xylose according to claim 6, it is characterized in that comprising following preparation process:
Corncob and oxalic acid are carried out ball milling, and then adding water is placed in microwave reaction kettle and reacts, and obtains the hydrolyzate containing wood sugar; Then be placed in reactor by containing the hydrolyzate of wood sugar, sulfonated charing corncob catalyst and carrene, at 160 ~ 180 DEG C of temperature, react 1.5 ~ 2.5h, product, through separation and purification, obtains furfural.
8. the method for a kind of sulfonated charing corncob catalyst Furfural Production from Xylose according to claim 7, is characterized in that: described is 5% ~ 7% containing the mass percentage of wood sugar in the hydrolyzate of wood sugar.
9. the method for a kind of sulfonated charing corncob catalyst Furfural Production from Xylose according to claim 7 or 8, is characterized in that: the described hydrolyzate containing wood sugar: sulfonated charing corncob catalyst: the ratio of the addition of carrene is (2 ~ 4) mL:(0.02 ~ 0.04) g:(4 ~ 8) mL.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106179404A (en) * | 2016-07-12 | 2016-12-07 | 江苏大学 | A kind of biomass carbon based solid acid for 5 Hydroxymethylfurfural synthesis and preparation method thereof |
| CN106423214A (en) * | 2016-08-22 | 2017-02-22 | 齐鲁工业大学 | Method for preparing carbon-based solid acid with high specific surface area and high acid content from corncob hydrolysis residues |
| CN108539213A (en) * | 2018-04-04 | 2018-09-14 | 广州大学 | A kind of corncob catalyst, the preparation method and microbiological fuel cell of Catalytic Layer |
| CN108727311A (en) * | 2018-05-14 | 2018-11-02 | 安徽理工大学 | A kind of furfural production new process of environmental protection |
| CN109384224A (en) * | 2017-08-02 | 2019-02-26 | 南京林业大学 | A kind of method that oil tea shell prepares xylose and furfural and coproduction medicinal carbon |
| CN114768828A (en) * | 2022-05-31 | 2022-07-22 | 陕西科技大学 | Carbon-based solid acid catalyst CS-SO3H, preparation method and application in preparation of furfural by biomass raw material conversion |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106179404A (en) * | 2016-07-12 | 2016-12-07 | 江苏大学 | A kind of biomass carbon based solid acid for 5 Hydroxymethylfurfural synthesis and preparation method thereof |
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| CN108727311A (en) * | 2018-05-14 | 2018-11-02 | 安徽理工大学 | A kind of furfural production new process of environmental protection |
| CN114768828A (en) * | 2022-05-31 | 2022-07-22 | 陕西科技大学 | Carbon-based solid acid catalyst CS-SO3H, preparation method and application in preparation of furfural by biomass raw material conversion |
| CN114768828B (en) * | 2022-05-31 | 2023-11-17 | 陕西科技大学 | Carbon-based solid acid catalyst CS-SO 3 H, preparation method and application thereof in preparing furfural by converting biomass raw materials |
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Application publication date: 20160420 |
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| RJ01 | Rejection of invention patent application after publication |