CN102212046A - Catalytic system for synthesizing 5-hydroxymethylfurfural by dehydration of sugar or polysaccharide - Google Patents
Catalytic system for synthesizing 5-hydroxymethylfurfural by dehydration of sugar or polysaccharide Download PDFInfo
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Abstract
The invention relates to a catalytic system for synthesizing 5-hydroxymethylfurfural by dehydration of sugar or polysaccharide. The catalytic system consists of metal halide and halogenated ammonium, wherein the molar ratio of metal halide to halogenated ammonium is 0.1-10; and the catalytic system is used for synthesizing 5-hydroxymethylfurfural by dehydration of sugar or polysaccharide. The specific method comprises the following steps: dissolving the sugar or polysaccharide in a solvent; adding the mixture into the catalytic system so as to form a reaction system; and at the temperature of 0-200 DEG C and under atmosphere gas, carrying out magnetic stirring for dehydration reaction, wherein the reaction time is 30 seconds to 24 hours. The catalytic system has the advantages that the components of the catalytic system are different halogenated compounds, raw materials are available and cheap and cost is low, can catalyze the dehydration of sugar or polysaccharide so as to prepare 5-hydroxymethylfurfural with high efficiency and high selectivity and is environmentally-friendly, and the product is easy to process; in the whole process, different sugar or polysaccharide compounds are consumed, and cost is low, thereby meeting the technical economy requirement and having a good application prospect.
Description
Technical field
The present invention relates to prepare the catalyzer of 5 hydroxymethyl furfural, particularly a kind of catalyst system that is used for sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration.
Background technology
At present, in order to solve energy dilemma and development low-carbon economy, in chemical field, gradually the catalysis biomass feedstock conversion is synthesized the high added value chemical as an important research direction.With sucrose and polysaccharide is that the synthetic furan derivatives of reaction raw materials is the main process that Wood Adhesives from Biomass is utilized, in general, molecule inner dewatering reaction takes place earlier in sucrose, after obtaining intermediate fructose and glucose, further the process three-step reaction forms the final product 5 hydroxymethyl furfural after sloughing trihyarol.U.S. Pat 4740605 has been reported the method with the synthetic 5-hydroxymethylfurans aldehyde of the aqueous solution of inorganic acid as catalyst high-temperature catalytic sugar compounds.Generate in the process of 5 hydroxymethyl furfural at sucrose and polysaccharide dehydration, catalyzer commonly used comprises mineral acid and solid acid.People such as Chheda find in the water/organic two-phase system that comprises water, DMSO and 7:3MIBK-2-butanols composition, with mineral acid (hydrochloric acid, sulfuric acid or phosphoric acid) when making catalyzer, compound generation dehydration reactions such as catalysis sucrose, starch, cellobiose and xylan effectively, and highly selective is prepared 5 hydroxymethyl furfural (Green Chem. 9 (2007) 342).People such as Ilgen are in the molten system of ChCl (choline chloride) and sugar compounds composition, use to benzene methanesulfonic acid as catalyzer, when inulin and sucrose were carried out catalytic and dehydration reaction, the yield of 5 hydroxymethyl furfural was 25% and 57% (Green Chem. 11 (2009) 1948) in the product.Binder and Raines back after deliberation find, with 6.0mol% sulfuric acid as catalyzer, when in the DMAc-KI solvent system polysaccharide and Mierocrystalline cellulose being carried out catalytic and dehydration reaction, the yield of product 5 hydroxymethyl furfural can reach 92% (J. Am. Chem. Soc. 131 (2009) 1979).People such as Ilgen are in the molten system of ChCl (choline chloride) and sugar compounds composition, use to benzene methanesulfonic acid as catalyzer, when inulin and sucrose are carried out catalytic and dehydration reaction, people such as product C arlini have reported with niobium phosphate and have made the dehydration results of catalyzer at aqueous phase catalysis sucrose and inulin, the productive rate of principal product 5 hydroxymethyl furfural be respectively 27% and 31%(Appl. Catal. A:Gen 183 (1999) 295).Chheda and Dumesic have then investigated the response situation of the synthetic 5 hydroxymethyl furfural of Diaion PK-216 resin catalysis inulin and sucrose dehydration in water-NMP two-phase system, found that, its reaction yield can reach 69% and 43% (Catalysis Today, 123 (2007) 59) respectively.Studies show that further, when using the Amberlyst-15 resin to make catalyzer, the yield of sucrose and the synthetic 5 hydroxymethyl furfural of inulin dehydration be respectively 27% and 54%(Green Chem. 11 (2009) 1948).Above-mentioned result of study shows, owing to have a large amount of fructose and glucose molecule structural unit in sucrose and the polysaccharide molecule, therefore, when reacting with single catalyst system, the selectivity of product 5 hydroxymethyl furfural is relatively poor, thereby cause productive rate lower, still need constantly to improve and improve the catalyzed reaction technology.
Summary of the invention
The objective of the invention is at above-mentioned technical Analysis, a kind of catalyst system that is used for sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration is provided, this catalyst system shows the characteristics of even phase catalyst fully in reaction process, the catalytic activity height, selectivity is higher and catalyst levels can be optimized to trace, helps the separation and the purifying of reaction product; Adopt the synthesis process of this catalyst system simple, aftertreatment is easy, production cost is low, safety no hidden danger and environmentally friendly.
Technical scheme of the present invention:
A kind of catalyst system that is used for sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration is made up of metal halide and two kinds of compounds of ammonium halide, and the mol ratio of metal halide and ammonium halide is 0.1-10.
Described metal halide is chromium chloride, chromium dichloride, aluminum chloride, tin chloride, tin protochloride, nickelous chloride, molybdenum chloride, chromic bromide, Tin tetrabromide, aluminum bromide, nickelous bromide, molybdenum bromide, iodate chromium, aluminum iodide or Tin tetraiodide.
Described ammonium halide is brometo de amonio, ammonium chloride, Neutral ammonium fluoride or ammonium iodide.
A kind of described application that is used for the catalyst system of sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration, be used for the reaction of the synthetic 5 hydroxymethyl furfural of sucrose or polysaccharide dehydration, method is: sucrose or polysaccharide are dissolved in the solvent, add this catalyst system and form reaction system, in temperature is 0-200 ℃ and atmosphere gas, magnetic agitation is carried out dehydration reaction, and the reaction times is 30 seconds-24 hours, can make 5 hydroxymethyl furfural.
Described polysaccharide is inulin, starch, xylan, seminose, cellobiose, lactose, Mierocrystalline cellulose or hemicellulose.
Described solvent be water,
N-methyl-2-pyrrolidone, dimethyl sulfoxide (DMSO),
N, N-dimethyl formamide,
N, N-N,N-DIMETHYLACETAMIDE, acetonitrile, ethanol, methyl alcohol, ethyl acetate, chloroform or chlorobenzene.
The molar percentage of catalyst system and sucrose or polysaccharide is 0.01-30mol% in the described reaction system, and the amount ratio of sucrose or polysaccharide and solvent for use is 1 g sucrose or polysaccharide/2-50mL solvent.
Described atmosphere gas is nitrogen, argon gas or air.
The described hydroxymethylfurfural that makes adopts the distillation method concentrated reaction solution, uses the ethyl acetate extraction mixing solutions then, after underpressure distillation, the drying, obtains high-purity hydroxymethylfurfural.
Advantage of the present invention is: the component of this catalyst system is different halogenated compound, and raw material is cheap and easy to get, and is with low cost; This catalyst system is used for the synthetic 5 hydroxymethyl furfural of sucrose or polysaccharide dehydration, can high-level efficiency, highly selective catalysis sucrose or polysaccharide dehydration preparation 5 hydroxymethyl furfural, environmental friendliness, product is handled easily; What whole process consumed is different sucrose or compound of polysaccharide, with low cost, can satisfy the requirement of Technological Economy, and good prospects for application is arranged.
Embodiment
Embodiment 1: the catalytic dehydration of sucrose
With 1.0g(5.6mmol) sucrose dissolved is in the 10mL dimethyl sulfoxide (DMSO), and adding 0.56mmol iron(ic) chloride and 0.28 mmol brometo de amonio are at 90 ℃, under the nitrogen protection, magnetic agitation was reacted after 2 hours, with the result of gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction; The transformation efficiency of sucrose is 98%, and the yield of 5 hydroxymethyl furfural can reach 75%.
Embodiment 2: the catalytic dehydration of cellobiose
The 1.0g cellobiose is dissolved in 20mL
N, NIn-the dimethyl formamide, add 0.45 mmol iron bromide and 0.30mmol ammonium chloride, at 80 ℃, under the oxygen atmosphere, magnetic agitation is reacted after 3 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The cellobiose transformation efficiency is 90%, and the yield of 5 hydroxymethyl furfural can reach 72%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 3: the catalytic dehydration of inulin
1.0 inulin are dissolved in 40mL
N-In the methyl-2-pyrrolidone, add 0.56mmol iron protochloride and 2.0mmol brometo de amonio, at 100 ℃, under the oxygen atmosphere, magnetic agitation is reacted after 3 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of inulin is 85%, and the yield of 5 hydroxymethyl furfural can reach 63%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 4: the catalytic dehydration of starch
1.0 g starch dissolutions in the 20mL high purity water, are added 0.56mmol iron(ic) chloride and 1.0mmol brometo de amonio, and at 80 ℃, under the air atmosphere, magnetic agitation is reacted after 5 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of starch is 82%, and the yield of 5 hydroxymethyl furfural can reach 5%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 5: the catalytic dehydration of xylan
1.0 g xylans are dissolved in the 40mL methanol solvate, add 0.14mmol ferric iodide and 0.25mmol brometo de amonio, at 110 ℃, under the nitrogen protection, magnetic agitation is reacted after 4 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of xylan is 75%, and the yield of 5 hydroxymethyl furfural can reach 21%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 6: the catalytic dehydration of seminose
The 1.0g seminose is dissolved in 50mL
N-In the methyl-2-pyrrolidone, add 0.56mmol iron(ic) chloride and brometo de amonio, at 90 ℃, under the nitrogen protection, magnetic agitation is reacted after 2 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The seminose transformation efficiency is 87%, and the yield of 5 hydroxymethyl furfural can reach 11%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 7: the catalytic dehydration of lactose
The 1.0g lactose is dissolved in the 10mL high purity water, adds 0.95mmol iron iodide and 1.25mmol brometo de amonio, at 100 ℃, under the nitrogen protection, magnetic agitation is reacted after 5 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of lactose can reach 84%, the yield 7% of 5 hydroxymethyl furfural; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 8: the catalytic dehydration of hemicellulose
The 1.0g hemicellulose is dissolved in 20mL
N, N-In the dimethyl formamide system, add 0.02mmol iron bromide and 0.05mmol ammonium chloride, at 100 ℃, under the air atmosphere, magnetic agitation is reacted after 3 hours 5 usefulness gas chromatograph-mass spectrometer (GC-MS)s and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of hemicellulose can reach 75%, the yield 18% of 5 hydroxymethyl furfural; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 9: cellulosic catalytic dehydration
With 1.0g(5.6mmol) Mierocrystalline cellulose is dissolved in the 10mL dimethyl sulfoxide (DMSO), adds 0.56mmol iron protochloride and 1.0mmol ammonium iodide, at 110 ℃, under the air atmosphere, magnetic agitation is reacted after 4 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; Cellulosic transformation efficiency can reach 53%, and the yield of 5 hydroxymethyl furfural is 10%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 10: the catalytic dehydration of sucrose
With 1.0g(5.6mmol) sucrose is dissolved in 2 mL
N, N-In the dimethyl formamide, add 0.56mmol iron(ic) chloride and 1.0mmol ammonium iodide, at 110 ℃, under the air atmosphere, magnetic agitation is reacted after 4 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of sucrose can reach 93%, and the yield of 5 hydroxymethyl furfural is 74%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 11: the catalytic dehydration of sucrose
With 1.0g(5.6mmol) sucrose is dissolved in the 5 mL dimethyl sulfoxide (DMSO), adds 0.56mmol ferrous bromide and 1.0mmol Neutral ammonium fluoride, and at 110 ℃, under the air atmosphere, magnetic agitation is reacted after 4 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of sucrose can reach 90%, and the yield of 5 hydroxymethyl furfural is 68%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Embodiment 12: cellulosic catalytic dehydration
The 1.0g Mierocrystalline cellulose is dissolved in 10mL
N-In the methyl-2-pyrrolidone, add 0.56mmol iron(ic) chloride and 1.0mmol brometo de amonio, at 110 ℃, under the air atmosphere, magnetic agitation is reacted after 4 hours, with gas chromatograph-mass spectrometer (GC-MS) and efficient liquid phase chromatographic analysis reaction result; The transformation efficiency of VITAMIN can reach 96%, and the yield of 5 hydroxymethyl furfural is 72%; After reaction finished, the distillation concentrated reaction solution was used the ethyl acetate extraction mixing solutions then, underpressure distillation, and drying is collected product.
Claims (9)
1. catalyst system that is used for the synthetic 5 hydroxymethyl furfural of sucrose or polysaccharide dehydration, it is characterized in that: be made up of metal halide and two kinds of compounds of ammonium halide, the mol ratio of metal halide and ammonium halide is 0.1-10.
2. according to the described catalyst system that is used for sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration of claim 1, it is characterized in that: described metal halide is chromium chloride, chromium dichloride, aluminum chloride, tin chloride, tin protochloride, nickelous chloride, molybdenum chloride, chromic bromide, Tin tetrabromide, aluminum bromide, nickelous bromide, molybdenum bromide, iodate chromium, aluminum iodide or Tin tetraiodide.
3. according to the described catalyst system that is used for sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration of claim 1, it is characterized in that: described ammonium halide is brometo de amonio, ammonium chloride, Neutral ammonium fluoride or ammonium iodide.
4. application that is used for the catalyst system of sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration according to claim 1, it is characterized in that: be used for the reaction of the synthetic 5 hydroxymethyl furfural of sucrose or polysaccharide dehydration, method is: sucrose or polysaccharide are dissolved in the solvent, add this catalyst system and form reaction system, in temperature is 0-200 ℃ and atmosphere gas, magnetic agitation is carried out dehydration reaction, and the reaction times is 30 seconds-24 hours, can make 5 hydroxymethyl furfural.
5. according to the described application that is used for the catalyst system of sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration of claim 4, it is characterized in that: described polysaccharide is inulin, starch, xylan, seminose, cellobiose, lactose, Mierocrystalline cellulose or hemicellulose.
6. according to the described application that is used for the catalyst system of the synthetic 5 hydroxymethyl furfural of sucrose or polysaccharide dehydration of claim 4, it is characterized in that: described solvent be water,
N-methyl-2-pyrrolidone, dimethyl sulfoxide (DMSO),
N, N-dimethyl formamide,
N, N-N,N-DIMETHYLACETAMIDE, acetonitrile, ethanol, methyl alcohol, ethyl acetate, chloroform or chlorobenzene.
7. according to the described application that is used for the catalyst system of sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration of claim 4, it is characterized in that: the molar percentage of catalyst system and sucrose or polysaccharide is 0.01-30mol% in the described reaction system, and the amount ratio of sucrose or polysaccharide and solvent for use is 1 g sucrose or polysaccharide/2-50mL solvent.
8. according to the described application that is used for the catalyst system of sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration of claim 4, it is characterized in that: described atmosphere gas is nitrogen, argon gas or air.
9. according to the described application that is used for the catalyst system of sucrose or the synthetic 5 hydroxymethyl furfural of polysaccharide dehydration of claim 4, it is characterized in that: the described hydroxymethylfurfural that makes adopts the distillation method concentrated reaction solution, use the ethyl acetate extraction mixing solutions then, after underpressure distillation, the drying, obtain high-purity hydroxymethylfurfural.
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| CN103483298A (en) * | 2013-10-14 | 2014-01-01 | 天津理工大学 | Method for preparing 5-hydroxymethylfurfural through efficient dehydration of hexose |
| JP2015526494A (en) * | 2012-09-03 | 2015-09-10 | アニッキ ゲーエムベーハーＡｎｎｉｋｋｉ Ｇｍｂｈ | Method for producing furan derivative |
| CN104923315A (en) * | 2015-05-29 | 2015-09-23 | 盐城工学院 | Solid acid catalyst TiP/ATP and preparation method and application thereof |
| CN105377825A (en) * | 2013-05-09 | 2016-03-02 | 诺瓦蒙特股份公司 | Process for the synthesis of 5-hydroxymethylfurfural from saccharides |
| CN109111414A (en) * | 2018-09-06 | 2019-01-01 | 沈阳化工大学 | A kind of method of agarose conversion coproduction 5 hydroxymethyl furfural and levulic acid |
| CN106279076B (en) * | 2015-05-20 | 2019-01-08 | 中国科学院宁波材料技术与工程研究所 | A method of catalysis hexose prepares 5 hydroxymethyl furfural |
| CN110229125A (en) * | 2019-07-25 | 2019-09-13 | 广西科学院 | A kind of low cost preparation method of sucrose base 5 hydroxymethyl furfural |
| CN113788805A (en) * | 2021-11-01 | 2021-12-14 | 沈阳化工大学 | Method for synthesizing hydroxymethylfurfural by lactose conversion |
| CN113906014A (en) * | 2019-06-06 | 2022-01-07 | 荷兰普拉克公司 | Method for producing hydroxymethylfurfural |
| CN114669310A (en) * | 2022-05-05 | 2022-06-28 | 中国科学院宁波材料技术与工程研究所 | Composite catalyst and synthetic method of bio-based furan chemical |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109111414A (en) * | 2018-09-06 | 2019-01-01 | 沈阳化工大学 | A kind of method of agarose conversion coproduction 5 hydroxymethyl furfural and levulic acid |
| CN113906014A (en) * | 2019-06-06 | 2022-01-07 | 荷兰普拉克公司 | Method for producing hydroxymethylfurfural |
| CN110229125A (en) * | 2019-07-25 | 2019-09-13 | 广西科学院 | A kind of low cost preparation method of sucrose base 5 hydroxymethyl furfural |
| CN110229125B (en) * | 2019-07-25 | 2022-04-19 | 广西科学院 | Low-cost preparation method of sucrose-based 5-hydroxymethylfurfural |
| CN113788805A (en) * | 2021-11-01 | 2021-12-14 | 沈阳化工大学 | Method for synthesizing hydroxymethylfurfural by lactose conversion |
| CN113788805B (en) * | 2021-11-01 | 2023-09-01 | 沈阳化工大学 | Method for synthesizing hydroxymethylfurfural through lactose conversion |
| CN114669310A (en) * | 2022-05-05 | 2022-06-28 | 中国科学院宁波材料技术与工程研究所 | Composite catalyst and synthetic method of bio-based furan chemical |
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Application publication date: 20111012 |