CN106905270A - A kind of technique for producing 5 hydroxymethylfurfurals - Google Patents
A kind of technique for producing 5 hydroxymethylfurfurals Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- 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
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- 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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Abstract
The present invention provides a kind of preparation method for preparing sulfonated graphene solid acid and its catalysis fructose produces the technique of 5 hydroxymethylfurfurals, and can effectively be catalyzed fructose by autonomous synthesis sulfonated graphene solid acid catalyst is dehydrated 5 hydroxymethylfurfurals of production.The sulfonated graphene preparation method that the present invention is provided is simple compared to conventional procedure, and preparation efficiency is high.Meanwhile, the fructose catalytic of high concentration can be converted into 5 hydroxymethylfurfurals by the technique that the present invention is provided with the sulfonated graphene solid acid of low dosage, and transformation efficiency is high, improve the economic feasibility of 5 hydroxymethylfurfurals production.
Description
Technical field
The present invention relates to solid catalyst field, the preparation method of particularly a kind of sulfonated graphene solid acid and sulfonation
The technique that Graphene solid acid catalysis fructose produces 5 hydroxymethyl furfural.
Background technology
Acidic catalyst suffers from important use in various fields such as the energy, chemical industry and synthesis.Compared to liquid acid catalysis
Agent, solid acid catalyst has can be reused and reduce the advantages such as equipment corrosion.Solid acid catalyst species is various, wherein
Carbon-based solid acid catalyst has chemical inertness, surface hydrophobic, good mechanical stability and heat endurance, therefore enjoys pass
Note.Carbon-based material miscellaneous, including activated carbon, biomass all may be used by the carbon-based material for being formed that is carbonized under hydrothermal conditions
For preparing carbon-based solid acid.These carbon-based solid acids have shown good catalysis and have lived in the reaction such as esterification and hydrolysis
Property.
Graphene is a class new carbon, obtains substantial amounts of concern.Graphene is to form two-dimentional material by individual layer atom
Material, with specific surface area is big, surface is easy to the characteristics such as modification.Graphene and its derived material are in nano composite material, Flied emission
There is huge application prospect in the fields such as material, sensing and energy storage material.In recent years, work(of the domestic and foreign scholars with regard to graphenic surface
Energyization has carried out numerous studies come the application model for improving the dispersiveness and dissolubility of Graphene so as to widen graphite alkenes material
Enclose.Due to the high-hydrophilic of sulfonic acid group, after carrying out sulfonation treatment to Graphene, its dispersiveness can be not only improved, can be with
Retain its unique property, so sulfonation has become one of modified study hotspot of Graphene.Current sulfonated graphene system
Standby often process is complicated, needs are carried out under specific condition, or uses poisonous go back original reagent, easily pollutes environment, hinders
Industrialization.Therefore, efficiently convenient, safety and environmental protection the high-quality sulfonated graphene for preparing is the technical barrier in the urgent need to capturing.
With continuing to develop for global economy, the fossil fuel such as oil progressively move towards exhaust.The exhaustion of fossil fuel is not
The shortage of the energy can be only brought, also means that modern organic industry loses most important carbon source based on this.Realize the mankind
The sustainable development of society, it is necessary to find substituting renewable resource.Biomass are the preferable replacements of fossil resource in theory
Product, biomass source is abundant and can continuously regenerate.Meanwhile, biomass recycling use process is neutral carbon, nothing
By being that biomass are used as into the energy, material and chemicals all without producing extra carbon emission.It is raw material preparationization with biomass
Intermediate is learned, and then obtains the energy, material and fine chemicals and have become the important channel for realizing sustainable development.In biology
In matter conversion process, it is an intermediate for key that glucide is dehydrated the 5 hydroxymethyl furfural to be formed.5 hydroxymethyl furfural can
As the substitute of many petrochemical intermediates, for producing resin, plastics, medicine and fuel, with huge application potential.
At present, by the fructose converting catalyst into 5 hydroxymethyl furfural both including the liquid acid such as sulfuric acid, hydrochloric acid, also including boiling
The solid acids such as stone, metal oxide, metal phosphate, the carbon material of sulfonation and strong-acid ion exchange resin.Wherein, mineral acid
Fructose converting rate and 5- hydroxyl first furfural yields higher can be realized as homogeneous catalyst with some transition metal salt materials,
But its deficiency is that catalyst is difficult to recycle, and easily causes equipment corrosion and environmental pollution.Zeolite and the carbon of sulfonation
The solid acid catalysts such as material can also obtain 5- hydroxyl first furfural yields higher, but because the structure of catalyst itself is limited
Contact of the avtive spot with reactant, limits reaction efficiency.During using solid acid catalyst, in order to obtain selectivity higher
The catalyst of high dose is generally needed to use, simultaneous reactions thing concentration will be kept low.In view of follow-up product point
From purifying and the recycling of catalyst, this is very uneconomic.Therefore, new catalyst is designed and developed, in low dosage
It is technical bottleneck in the urgent need to address that the reactant of high concentration is converted into 5 hydroxymethyl furfural under catalyst action.
The content of the invention
It is an object of the invention to solve to overcome traditional carbon-based solid acid and sulfonated graphene solid acid preparation process multiple
It is miscellaneous, easily cause the deficiencies such as environmental pollution, and 5 hydroxymethyl furfural low production efficiency shortcoming.A kind of one kettle way is provided to prepare
The method of sulfonated graphene solid acid and by fructose Efficient Conversion for 5- hydroxyl first furfurals technique.
The preparation method of the sulfonated graphene solid acid that the present invention is provided, comprises the following steps：
(1) under condition of ice bath, by the concentrated sulfuric acid and SPA according to mass ratio 8 ~ 20:1 is well mixed, and obtains mixed acid solution；
(2) under the stirring of 200-1200 r/min, 1-6 mass parts are separately added into the mixed acid solution to 400 mass parts
The sodium nitrate of graphite powder and 0.5-3 mass parts；
(3) keep reaction temperature below 20 DEG C, the reactant mixture obtained to step (2) adds the height of 10-20 mass parts
Potassium manganate, is progressively warmed up to 50 DEG C after being well mixed, react 24h；
(4) room temperature is cooled to, the hydrogenperoxide steam generator of 3-60 mass parts is added, 0.2-2h is stirred；
(5) solid material for obtaining is reacted by centrifugation, is washed with watery hydrochloric acid, water and ethanol respectively, be finally dried to obtain
Sulfonated graphene.
The use low dosage solid acid that the present invention is provided by high concentration it is fructose converting be 5 hydroxymethyl furfural, including following step
Suddenly：
(1) by ionic liquid and auxiliary agent according to mass ratio 1 ~ 10:5 are mixed, and obtain mixed solvent；
(2) to the sulfonated graphene that 0.5-1.5 mass parts are added in the mixed solvent of 100 mass parts, in the microwave of 200-800W
Ultrasound 10-60 minutes under power；
(3) to the fructose that 5-25 mass parts are added in above-mentioned system, 100-140 DEG C is heated to, is reacted 30-180 minutes；
(4) reaction terminate after catalyst is recovered by centrifugation, by extraction and distillation be separately recovered 5 hydroxymethyl furfural product and
Solvent.
Ionic liquid used by the present invention is glyoxaline ion liquid, the pyridines ionic liquid that can dissolve glucide
Body, pyrrolidines ionic liquid, quaternary phosphonium salt ionic liquid and ion liquid of quaternaries, anion can be Cl-, Br-,
OAc-、CH3SO4、NTf2、BF4、PF6In one kind；
The auxiliary agent be alcohol, ketone, phenol, carboxylic acid, aldehyde, second eyeball, at least one in dimethyl alum,
Preferably, the alcohol is methyl alcohol, ethanol, isopropanol, n-butanol, isobutanol, the tert-butyl alcohol, propane diols, glycerine, chloroethene
Alcohol, at least one in phenmethylol；
The ketone is acetone, butanone, at least one in 2 pentanone；
The phenol is phenol, 2- chlorophenols, at least one in 2- cresols；
The shuttle acid is formic acid, acetic acid, at least one in propionic acid；
The aldehyde is formaldehyde, at least one in acetaldehyde.
The advantages of the present invention are：Prepared by single step reaction and be loaded with the sulfonic sulfonated graphite of high concentration
Alkene, preparation process is simple and convenient, reduces environmental pollution, can be by the fructose of high concentration using the sulfonated graphene of relatively low-dose
5 hydroxymethyl furfural is converted into, reaction conversion ratio and selectivity are high, are favorably improved the economy of 5- hydroxyl first furfural productions.
Specific embodiment
The present invention is described in further detail by following examples, but the technology contents that are described of the present embodiment be it is illustrative,
Rather than limited, protection scope of the present invention should not be limited to according to this.
Embodiment 1：
A kind of preparation method of sulfonated graphene solid acid, comprises the following steps：
(1) under condition of ice bath, by the concentrated sulfuric acid and SPA according to mass ratio 9:1 is well mixed, and obtains mixed acid solution；
(2) under the stirring of 600 r/min, the graphite powder of 3 mass parts is separately added into the mixed acid solution to 400 mass parts
With the sodium nitrate of 1.5 mass parts；
(3) keep reaction temperature below 20 DEG C, the reactant mixture obtained to step (2) adds the permanganic acid of 9 mass parts
Potassium, is progressively warmed up to 50 DEG C after being well mixed, react 24h；
(4) room temperature is cooled to, the hydrogenperoxide steam generator of 30 mass parts is added, 0.5h is stirred；
(5) solid material for obtaining is reacted by centrifugation, is washed with watery hydrochloric acid, water and ethanol respectively, be finally dried to obtain
Sulfonated graphene.Sulfonic content is 1.62 mMs every gram in sulfonated graphene.
Using low dosage solid acid by high concentration it is fructose converting be the technique of 5- hydroxyl first furfurals, comprise the following steps：
(1) by the methylimidazole (AMIMCl) of ionic liquid chlorination 1- pi-allyls -3 and auxiliary agent dimethyl sulfoxide (DMSO) (DMSO) according to quality
Than 1:1 is mixed, and obtains mixed solvent；
(2) to the sulfonated graphene that 1 mass parts are added in the mixed solvent of 100 mass parts, the ultrasound under the microwave power of 400W
10 minutes；
(3) to the fructose that 20 mass parts are added in above-mentioned system, 120 DEG C are heated to, are reacted 60 minutes；
(4) reaction terminate after catalyst is recovered by centrifugation, by extraction and distillation be separately recovered 5 hydroxymethyl furfural product and
Solvent.5 hydroxymethyl furfural yield is 68%.
Embodiment 2：
A kind of preparation method of sulfonated graphene solid acid, comprises the following steps：
(1) under condition of ice bath, by the concentrated sulfuric acid and SPA according to mass ratio 9:1 is well mixed, and obtains mixed acid solution；
(2) under the stirring of 600 r/min, the graphite powder of 3 mass parts is separately added into the mixed acid solution to 400 mass parts
With the sodium nitrate of 1.5 mass parts；
(3) keep reaction temperature below 20 DEG C, the reactant mixture obtained to step (2) adds the permanganic acid of 18 mass parts
Potassium, is progressively warmed up to 50 DEG C after being well mixed, react 24h；
(4) room temperature is cooled to, the hydrogenperoxide steam generator of 30 mass parts is added, 0.5h is stirred；
(5) solid material for obtaining is reacted by centrifugation, is washed with watery hydrochloric acid, water and ethanol respectively, be finally dried to obtain
Sulfonated graphene.Sulfonic content is 1.62 mMs every gram in sulfonated graphene.
Using low dosage solid acid by high concentration it is fructose converting be the technique of 5- hydroxyl first furfurals, comprise the following steps：
(1) by the methylimidazole (AMIMCl) of ionic liquid chlorination 1- pi-allyls -3 and auxiliary agent dimethyl sulfoxide (DMSO) (DMSO) according to quality
Than 1:1 is mixed, and obtains mixed solvent；
(2) to the sulfonated graphene that 1 mass parts are added in the mixed solvent of 100 mass parts, the ultrasound under the microwave power of 400W
10 minutes；
(3) to the fructose that 5 mass parts are added in above-mentioned system, 120 DEG C are heated to, are reacted 60 minutes；
(4) reaction terminate after catalyst is recovered by centrifugation, by extraction and distillation be separately recovered 5 hydroxymethyl furfural product and
Solvent.5 hydroxymethyl furfural yield is 95%.
Embodiment 3：
A kind of preparation method of sulfonated graphene solid acid, comprises the following steps：
(1) under condition of ice bath, by the concentrated sulfuric acid and SPA according to mass ratio 9:1 is well mixed, and obtains mixed acid solution；
(2) under the stirring of 600 r/min, the graphite powder of 3 mass parts is separately added into the mixed acid solution to 400 mass parts
With the sodium nitrate of 1.5 mass parts；
(3) keep reaction temperature below 20 DEG C, the reactant mixture obtained to step (2) adds the permanganic acid of 9 mass parts
Potassium, is progressively warmed up to 50 DEG C after being well mixed, react 24h；
(4) room temperature is cooled to, the hydrogenperoxide steam generator of 30 mass parts is added, 0.5h is stirred；
(5) solid material for obtaining is reacted by centrifugation, is washed with watery hydrochloric acid, water and ethanol respectively, be finally dried to obtain
Sulfonated graphene.Sulfonic content is 1.31 mMs every gram in sulfonated graphene.
Using low dosage solid acid by high concentration it is fructose converting be the technique of 5- hydroxyl first furfurals, comprise the following steps：
(1) by the methylimidazole (AMIMCl) of ionic liquid chlorination 1- pi-allyls -3 and auxiliary agent dimethyl sulfoxide (DMSO) (DMSO) according to quality
Than 1:1 is mixed, and obtains mixed solvent；
(2) to the sulfonated graphene that 1 mass parts are added in the mixed solvent of 100 mass parts, the ultrasound under the microwave power of 400W
10 minutes；
(3) to the fructose that 5 mass parts are added in above-mentioned system, 120 DEG C are heated to, are reacted 60 minutes；
(4) reaction terminate after catalyst is recovered by centrifugation, by extraction and distillation be separately recovered 5 hydroxymethyl furfural product and
Solvent.5 hydroxymethyl furfural yield is 89%.
Claims (2)
1. a kind of technique for producing 5 hydroxymethyl furfural, it is characterised in that：It is dehydrated using sulfonated graphene solid acid catalysis fructose
Production 5 hydroxymethyl furfural is comprised the following steps：
(1) by ionic liquid and auxiliary agent according to mass ratio 1 ~ 10:5 are mixed, and obtain mixed solvent；
(2) to the sulfonated graphene that 0.5-1.5 mass parts are added in the mixed solvent of 100 mass parts, in the microwave of 200-800W
Ultrasound 10-60 minutes under power；
(3) to the fructose that 5-25 mass parts are added in above-mentioned system, 100-140 DEG C is heated to, is reacted 30-180 minutes；
(4) reaction terminate after catalyst is recovered by centrifugation, by extraction and distillation be separately recovered 5 hydroxymethyl furfural product and
Solvent.
2. a kind of technique for producing 5 hydroxymethyl furfural according to claim 1, it is characterised in that：Described sulfonated graphite
The preparation method of alkene solid acid is comprised the following steps：
(1) under condition of ice bath, by the concentrated sulfuric acid and SPA according to mass ratio 8 ~ 20:1 is well mixed, and obtains mixed acid solution；
(2) under the stirring of 200-1200 r/min, 1-6 mass parts are separately added into the mixed acid solution to 400 mass parts
The sodium nitrate of graphite powder and 0.5-3 mass parts；
(3) keep reaction temperature below 20 DEG C, the reactant mixture obtained to step (2) adds the height of 10-20 mass parts
Potassium manganate, is progressively warmed up to 50 DEG C after being well mixed, react 24h；
(4) room temperature is cooled to, the hydrogenperoxide steam generator of 3-60 mass parts is added, 0.2-2h is stirred；
(5) solid material for obtaining is reacted by centrifugation, is washed with watery hydrochloric acid, water and ethanol respectively, be finally dried to obtain
Sulfonated graphene.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997275A (en) * | 2018-06-20 | 2018-12-14 | 昆明理工大学 | A method of primary product distribution in control fructose-ethanol synthesis system |
| CN109776459A (en) * | 2019-02-27 | 2019-05-21 | 天津大学 | A kind of method that the fructose dehydration of hydrophobic solid acid catalysis prepares 5 hydroxymethyl furfural |
| CN115304565A (en) * | 2022-02-22 | 2022-11-08 | 南开大学 | Method for preparing 5-ethoxymethylfurfural by using porous carbon-based solid acid catalysis |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102199136A (en) * | 2011-03-31 | 2011-09-28 | 中国科学院西双版纳热带植物园 | Method for preparing 5-hydroxymethylfurfural from acidic iron liquids |
| CN104725204A (en) * | 2015-02-14 | 2015-06-24 | 嘉兴润博化工科技有限公司 | Method for producing 2-alkylanthraquinone with sulfonated graphene catalyst |
| CN104971772A (en) * | 2015-06-08 | 2015-10-14 | 天津工业大学 | Preparation method of sulfonic acid and thioether synergistic hybrid graphene catalyst |
-
2017
- 2017-03-16 CN CN201710155294.9A patent/CN106905270A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102199136A (en) * | 2011-03-31 | 2011-09-28 | 中国科学院西双版纳热带植物园 | Method for preparing 5-hydroxymethylfurfural from acidic iron liquids |
| CN104725204A (en) * | 2015-02-14 | 2015-06-24 | 嘉兴润博化工科技有限公司 | Method for producing 2-alkylanthraquinone with sulfonated graphene catalyst |
| CN104971772A (en) * | 2015-06-08 | 2015-10-14 | 天津工业大学 | Preparation method of sulfonic acid and thioether synergistic hybrid graphene catalyst |
Non-Patent Citations (1)
| Title |
|---|
| QIDONG HOU ET AL.: "One-pot synthesis of sulfonated graphene oxide for efficient conversion of fructose into HMF", 《RSC ADV.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997275A (en) * | 2018-06-20 | 2018-12-14 | 昆明理工大学 | A method of primary product distribution in control fructose-ethanol synthesis system |
| CN109776459A (en) * | 2019-02-27 | 2019-05-21 | 天津大学 | A kind of method that the fructose dehydration of hydrophobic solid acid catalysis prepares 5 hydroxymethyl furfural |
| CN115304565A (en) * | 2022-02-22 | 2022-11-08 | 南开大学 | Method for preparing 5-ethoxymethylfurfural by using porous carbon-based solid acid catalysis |
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Application publication date: 20170630 |