CN113968776A - Method for preparing cyclopentanone from biomass raw material - Google Patents
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- C07—ORGANIC CHEMISTRY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
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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
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
- B01J27/13—Platinum group metals
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- 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
- C07D307/42—Singly bound oxygen atoms
- C07D307/44—Furfuryl alcohol
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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
- 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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- 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
- C07D307/50—Preparation from natural products
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Abstract
The invention discloses a method for preparing cyclopentanone from a biomass raw material, and belongs to the field of fine chemical preparation. The system is a chloride or bromide aqueous solution system and an organic solvent system, the catalyst is a supported noble metal catalyst, and the high-yield cyclopentanone can be prepared from hemicellulose, xylan, xylose and arabinose in the original biomass in one step under certain reaction conditions. The method has the advantages of mild reaction temperature, environment-friendly system and sustainable raw material, and provides a novel method for preparing cyclopentanone from biomass raw material.
Description
Technical Field
The invention relates to a method for preparing cyclopentanone, in particular to a method for preparing cyclopentanone from hemicellulose components and saccharides in biomass in a one-step high-yield manner by taking hemicellulose components, xylan, xylose and arabinose in the biomass as raw materials and adopting an A/B supported noble metal catalyst, a chloride or bromide aqueous solution and an organic solvent two-phase reaction system under certain conditions.
Background
Cyclopentanone is an important organic intermediate and plays an important role in the fields of chemical industry, medicine, pesticide and energy. Meanwhile, cyclopentanone can also prepare polycyclic alkane through aldol condensation reaction, and the product has higher octane number and higher energy density than ethanol, and can be used as a biofuel for replacing gasoline.
The current industrial preparation method of cyclopentanone is mainly carried out by a process of using adipic acid as a raw material and barium hydroxide as a catalyst. The above methods still have many disadvantages in terms of both environmental friendliness and preparation cost. Particularly, adipic acid is used as a raw material of the method, and is derived from fossil energy, so that the method is not beneficial to quickly realizing two targets of carbon peak reaching and carbon neutralization in China. In comparison, biomass is a high-quality resource with wide distribution, low cost, neutral carbon and reproducibility, and it is very necessary to develop a method for preparing cyclopentanone from biomass raw materials.
In recent years, most of the reported research results for preparing cyclopentanone from biomass raw materials include furfural as a reaction raw material. As described in 2021, Hu and its colleagues continuously reported Ni/SiO in the research field of cyclopentanone preparation2And Ni-P/Al2O3The catalyst shows higher activity in the reaction of preparing cyclopentanone from furfural (Hongli Tian, Xun Hu, etc. molecular. Catal.510(2021) 111697; gumming Gao, Xun Hu, etc. Catal. Sci. technol.11(2021) 575.). Furfural, as a biomass platform compound, is hydrolyzed from hemicellulose, or xylan and xylose in biomass at high temperature. SnO reported by Zhang and coworkers as 2021xConversion of xylose to bran based catalystIn the work of aldehyde, xylose is successfully converted into furfural at the reaction temperature of 180 ℃ (NanZhou, Shicheng Zhang, etc. j. cleaner. production.311(2021)127780), the method has the advantages of high reaction temperature and low xylose conversion furfural efficiency (furfural yield of 53.9%) due to the easy polymerization of high-concentration furfural; in the work reported by Wang and colleagues in 2021, in which xylose is converted into cyclopentanone by solid acid catalysis on a carbon carrier (Hao Xu, Shurong Wang, etc. energy Fuel 35(2021)9961), the reaction temperature with better activity is considerable 170 ℃, and furfural yield (84.9% of furfural yield) is obtained, even though heat energy loss is inevitable in the process of preparing furfural by xylose conversion. The cyclopentanone is prepared by directly utilizing more original biomass raw materials such as xylose, xylan and even original biomass through one-step conversion, so that the heat energy loss is avoided, and the energy utilization efficiency is particularly important to be improved.
Disclosure of Invention
The reaction of the invention starts from more original biomass materials (xylose, xylan and protoplasm), and converts reaction raw materials into cyclopentanone in one step by using two reaction systems of chloride salt or bromide aqueous solution/organic solvent and adopting an A/B supported noble metal catalyst in a hydrogen atmosphere. Integrating a plurality of reactions such as hemicellulose, xylose hydrolysis to generate xylose, furfural dehydration and isomerization to generate furfural, and selective hydrogenation and isomerization of furfural to generate cyclopentanone. The addition of chloride or bromide has an important effect, and the catalyst not only can promote the hydrolysis of hemicellulose or xylan in the original biomass, but also has the functions of promoting the selective hydrogenation of C ═ O in furfural by an A/B supported noble metal catalyst to generate furfuryl alcohol and promoting the isomerization of the furfuryl alcohol to generate cyclopentanone. Cl and Br have poisoning effect on the noble metal catalyst, and the catalyst can be catalyzed by poisoning A/B supported noble metal to weaken the hydrogenation capability of the catalyst on C ═ C, and selectively hydrogenate C ═ O, so that furfural is promoted to generate furfuryl alcohol, namely a main intermediate for generating cyclopentanone; moreover, the halogen ions have the function similar to Lewis acid and can promote the isomerization of furfuryl alcohol to cyclopentanone. And the organic solvent in the reaction system can extract the organic phase in time in the reaction process to separate the product from the water phase, thereby not only promoting the forward proceeding of the sugar conversion reaction in the water phase, but also avoiding the complex procedure of product separation in the later period to a certain extent.
The invention aims to provide a method for preparing cyclopentanone by hydrolyzing, hydrogenating and isomerizing a biomass raw material, which is realized by the following technical means:
a method for preparing cyclopentanone from biomass raw materials adopts a chloride or bromide aqueous solution/organic solvent two-phase reaction system and adopts an A/B supported noble metal catalyst in a hydrogen atmosphere to directly convert the reaction raw materials into the cyclopentanone in one step.
Further, in the above technical solution, the aqueous solution of chloride or bromide salt includes an aqueous solution of a mixture of one or more of sodium chloride, sodium bromide, potassium chloride, and potassium bromide.
Further, in the technical scheme, the mass concentration range of the chloride salt or bromide salt aqueous solution is 10-30%.
Further, in the above technical solution, the organic solvent includes one or a mixture of two or more of toluene, methyl isobutyl ketone, cyclohexane, methylcyclohexane, and tetrahydrofuran.
Further, in the above technical scheme, the reaction raw material comprises one or a mixture of more than two of hemicellulose components, xylan, xylose and arabinose in the raw biomass.
Further, in the above technical scheme, the raw biomass comprises one or a mixture of more than two of wood, corncob and straw.
Further, in the above technical solution, the a/B supported noble metal is a catalyst, wherein a includes one or a mixture of two or more of Pt, Pd, and Ru; b comprises one or a mixture of more than two of active carbon, silicon oxide and aluminum oxide; wherein the mass loading of A is 0.5-10%.
Further, in the technical scheme, the reaction is carried out in a reaction kettle, the reaction temperature is 130-220 ℃, the hydrogen pressure is 0.5-5 MPa, and the reaction time is 0.5-24 hours.
The method has the advantages that: the method for preparing cyclopentanone from biomass and the platform compound thereof has the advantages of high reaction yield, high selectivity, mild conditions, low raw material cost, environment-friendly and sustainable process, and provides a new method for preparing cyclopentanone. The raw materials (xylose, xylan and native biomass) used in the invention are reproducible, widely distributed and low in price; the sodium chloride aqueous solution with the best performance in the chloride or bromide aqueous solution in the reaction is used as the main component of the seawater, and has the advantages of wide distribution, easy obtaining, low price, regeneration and the like. The whole reaction process is acid-free and alkali-free, has no great corrosivity on reaction equipment, and is beneficial to large-scale production. In summary, compared with the prior pentanone preparation method (including fossil energy reaction route and biomass reaction route), the method has the advantages of easily available raw materials, simple process, low heat energy consumption, high production efficiency and the like. Has great significance for sustainable development of energy in China, environmental protection and rapid realization of the strategic goals of carbon neutralization and carbon peak reaching.
Drawings
FIG. 1 is a gas chromatogram of the preparation of cyclopentanone according to example 1.
FIG. 2 is a mass spectrum of cyclopentanone prepared in example 1.
Detailed Description
The following non-limiting examples will allow one of ordinary skill in the art to more fully understand the present invention, but are not intended to limit the invention in any way.
Examples 1 to 4
1g of xylose was added to a 50mL reaction vessel, 100mg of Ru/C with a mass loading of 5% was added as a catalyst, and 10mL of a 10% by mass aqueous solution of a chloride or bromide salt and 20mL of toluene were added. Hydrogen gas of 3MPa is added, and the reaction is carried out for 4 hours at 160 ℃.
TABLE 1 summary of the results of the preparation of cyclopentanone from various salt solutions
In examples 1 to 4, sodium chloride, sodium bromide, potassium chloride and potassium bromide can all promote xylose to be converted into cyclopentanone, wherein the yield of cyclopentanone in a sodium chloride aqueous solution toluene catalysis system reaches 63%.
Examples 5 to 9
1g of xylose is added into a 50mL reaction kettle, 100mg of Ru/C with the mass loading of 5% is added as a catalyst, and 10mL of sodium chloride aqueous solution with different mass concentrations and 20mL of toluene are added. Hydrogen gas of 3MPa is added, and the reaction is carried out for 4 hours at 160 ℃.
TABLE 2 summary of the results of the preparation of cyclopentanone from aqueous sodium chloride solutions of various concentrations
Examples 5 to 9 show that the addition of the sodium chloride aqueous solution can indeed promote the conversion of xylose into cyclopentanone, and that the yield of cyclopentanone can reach 63% under the action of the 10% by mass sodium chloride aqueous solution.
Examples 10 to 15
Pulverizing poplar, corncob and wheat straw, drying xylan, xylose and arabinose, respectively adding 1g of the pulverized poplar, corncob and wheat straw into a 50mL reaction kettle, adding 10mg of Ru/C with the mass loading of 5% as a catalyst, and adding 10mL of a chloride or bromide aqueous solution with the mass concentration of 10% and 20mL of toluene. Hydrogen gas of 3MPa was introduced, and the reaction was carried out at 200 ℃ for 4 hours.
TABLE 3 summary of the results of the preparation of cyclopentanone from different starting materials
Examples 10 to 15 show that cyclopentanone can be prepared from the above-mentioned various raw materials by this method, and that a yield of cyclopentanone of about 30% can be obtained even when raw materials such as poplar, corn cob or wheat straw are used. And when xylose was used as a reaction substrate, the yield of cyclopentanone reached 63%.
Examples 16 to 20
1g of xylose is added into a 50mL reaction kettle, 10mg of Ru/C with the mass loading of 5% is added as a catalyst, and 10mL of a chloride or bromide aqueous solution with the mass concentration of 10% and 20mL of an organic solvent are added. Hydrogen gas of 3MPa is added, and the reaction is carried out for 4 hours at 160 ℃.
TABLE 4 summary of the results of the preparation of cyclopentanone from fructose under the influence of different organic solvents
Examples 16-20 show that xylose can be converted to cyclopentanone under these conditions when the organic solvent is selected from toluene, methyl isobutyl ketone, cyclohexane, methylcyclohexane, and tetrahydrofuran. When toluene is selected as the organic solvent, the yield of cyclopentanone can reach 63%.
Examples 21 to 29
1g of xylose was charged into a 50mL reactor, 100mg of a 5% by mass supported catalyst was added, and 10mL of a 10% by mass aqueous solution of a chloride or bromide salt and 20mL of toluene were added. Hydrogen gas of 3MPa is added, and the reaction is carried out for 4 hours at 160 ℃.
TABLE 5 summary of the results of the preparation of cyclopentanone from fructose under the influence of different noble metal catalysts
Examples 21-29 show that xylose can be converted to cyclopentanone under the action of the above catalyst. When Ru/C is selected as the catalyst, the yield of cyclopentanone can reach 63%.
Examples 30 to 36
Adding 1g of xylose into a 50mL reaction kettle, adding 100mg of Ru/C catalyst with the mass loading of 0.1-10%, and adding 10mL of chloride or bromide aqueous solution with the mass concentration of 10% and 20mL of toluene. Hydrogen gas of 3MPa is added, and the reaction is carried out for 4 hours at 160 ℃.
TABLE 5 summary of the results of the preparation of cyclopentanone from fructose under the influence of different noble metal catalysts
Examples 30-36 show that the reaction begins to show selectivity to cyclopentanone when the active component loading in the Ru/C catalyst is 0.5% and above. At a mass loading of 5% Ru, cyclopentanone yield reached a maximum of 63%.
Examples 37 to 46
1g of xylose was charged into a 50mL reaction vessel, 100mg of Ru/C with a mass loading of 5% was added as a catalyst, and 10mL of a 10% by mass aqueous solution of a chloride or bromide salt and 20mL of toluene were added. Hydrogen gas of 3MPa is added, and the reaction is carried out for 4 hours at different temperatures.
TABLE 6 summary of the results of the preparation of cyclopentanone from fructose under the influence of different reaction temperatures
In examples 37 to 46, it can be seen that, at the above reaction temperature, xylose can be converted to prepare cyclopentanone, and an optimal process can be achieved when the reaction temperature is 160 ℃, and the yield of cyclopentanone can reach 63%.
Examples 47 to 52
1g of xylose was charged into a 50mL reaction vessel, 100mg of Ru/C with a mass loading of 5% was added as a catalyst, and 10mL of a 10% by mass aqueous solution of a chloride or bromide salt and 20mL of toluene were added. Hydrogen gas was introduced under pressure, and the reaction was carried out at 160 ℃ for 4 hours.
TABLE 7 summary of the results of fructose preparation of cyclopentanone under the influence of different hydrogen pressures
In examples 47 to 52, it can be seen that, in the hydrogen atmosphere with the above pressure, xylose can be converted to prepare cyclopentanone, and when the hydrogen pressure is 3MPa, an optimal process can be achieved, and the yield of cyclopentanone can reach 63%.
Examples 53 to 58
1g of xylose was charged into a 50mL reaction vessel, 100mg of Ru/C with a mass loading of 5% was added as a catalyst, and 10mL of a 10% by mass aqueous solution of a chloride or bromide salt and 20mL of toluene were added. 3MPa hydrogen is added, and the reaction is carried out for a certain time at 160 ℃.
TABLE 8 summary of the results of the preparation of cyclopentanone from fructose under the influence of different reaction temperatures
Examples 53-58 show that xylose can be converted to cyclopentanone at the above reaction time, and the reaction is in equilibrium when the reaction time is 4 hours.
Claims (8)
1. A method for preparing cyclopentanone from biomass raw materials is characterized by comprising the following steps:
adopting a chloride or bromide aqueous solution/organic solvent two-phase reaction system, and adopting an A/B supported noble metal catalyst in a hydrogen atmosphere to directly convert reaction raw materials into cyclopentanone in one step;
the reaction raw material comprises one or a mixture of more than two of hemicellulose components, xylan, xylose and arabinose in the original biomass.
2. The method of claim 1, wherein:
the aqueous solution of the chloride salt or the bromide salt comprises an aqueous solution of a mixture of one or more of sodium chloride, sodium bromide, potassium chloride and potassium bromide.
3. The method of claim 1, wherein:
the organic solvent comprises one or a mixture of more than two of toluene, methyl isobutyl ketone, cyclohexane, methylcyclohexane and tetrahydrofuran.
4. The method of claim 1, wherein:
the mass concentration range of the chloride or bromide aqueous solution is 10-30%.
5. The method of claim 1, wherein:
the raw biomass comprises one or a mixture of more than two of wood, corncob and straw.
6. The method of claim 1, wherein:
the A/B supported noble metal is a catalyst, wherein A comprises one or a mixture of more than two of Pt, Pd and Ru; b comprises one or a mixture of more than two of active carbon, silicon oxide and aluminum oxide; wherein the mass loading of A is 0.5-10%.
7. The method of claim 1, wherein:
the reaction temperature is 130-220 ℃, the hydrogen pressure is 0.5-5 MPa, and the reaction time is 0.5-24 hours.
8. The method of any one of claims 1-7 utilizing a biomass feedstock to produce the resultant cyclopentanone.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2022242730A1 (en) * | 2021-05-21 | 2022-11-24 | 中国石油化工股份有限公司 | Method for preparing 2, 5-hexanedione by catalyzing and converting biomass by one-pot synthesis |
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2021
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| CN103159606A (en) * | 2011-12-12 | 2013-06-19 | 中国科学院大连化学物理研究所 | Method for preparing cyclopentanone by using furaldehyde as raw material |
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