CN111732977A - Method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein - Google Patents
Method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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Abstract
A method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein comprises dissolving furylacrolein in fatty alcohol, adding supported nano metal catalyst, heating to 150-350 deg.C, and reacting to obtain furan alcohol biodiesel; the metal in the supported nano metal catalyst comprises one or more of nickel, iron, cobalt, palladium and ruthenium, and the carrier is nano porous carbon. The preparation method provided by the invention has the advantages of small catalyst consumption, high product yield, easiness in separation, no need of additional hydrogen in the reaction process, low production cost, safety, no hidden danger and environmental friendliness.
Description
Technical Field
The invention relates to a method for effectively utilizing biomass-based furfural derived aldehyde, in particular to a method for preparing furan alcohol biodiesel by in-situ hydrogenation of furan-based acrolein.
Background
Since the industrial revolution, the rapid development of the petrochemical industry promotes the unprecedented prosperity of social economy and also helps the transportation industry to fly. However, a series of problems such as fossil energy shortage, environmental pollution, climate deterioration and the like become considerable challenges in the civilized society, development of clean energy, improvement of energy structure, guarantee of energy safety, and vigorous promotion of ecological civilized construction become common recognition among international organizations, and are also necessary to be the work center of governments for a long period of time in the future. Meanwhile, the utilization of a large amount of renewable energy resources represented by biomass is in need of new and greater development and efficient utilization. Therefore, the potential of using biomass as a green feedstock for the production of high-grade fuels remains to be further explored, see: j chedda, g.huber and j.dumesic.angelw Chem Int Ed engl.j.2007,46,7164; n.n.kuznetsov, n.v.chesnoov, o.v.yatsenkova, et al.j.russian chemical bulletin,2013,62,1493; serrano-Ruiz, j.a.dumesic, Energy environ.sci.,2011,4, 83. The biomass is used as a carbon-containing organic matter macromolecular functional body which is most widely existed and most abundant in the nature, and agricultural and forestry wastes such as lignocellulose and the like are converted into degradable high-value-added chemicals and functional carbon materials or high-efficiency clean fuels by utilizing biological manufacturing and biomass refining technologies, so that great advantages are brought to the solution of environmental pollution, energy shortage and transformation and upgrading of materials. Preparing energy to make up for the gap of fossil energy is the most promising direction of utilization of biomass.
Furfural has historically received widespread attention as an important biomass-based platform molecular compound with annual yields of over 1000000 tons, see Biorefineries-Industrial Processes and Products, ed.b. kamm, p.r. gruber and m.kamm, Wiley-VCH, Weinheim, 2006. In recent years, the technology for preparing the furylacrolein with an increased carbon chain by utilizing (oxidation) condensation of furfural and short-carbon-chain micromolecule compounds such as aldehyde, ketone, fatty alcohol and the like is gradually improved, a process for preparing the high-calorific-value biodiesel by hydrogenating and deoxidizing the furylacrolein is developed, the ecological environment is protected, the consumption of primary resources such as petroleum is reduced, and the method is an important way for realizing the conversion of biomass-based furfural derivatives to high-value-added industrial chemicals, and is shown in the followings: j. Zeitsch, The Chemistry and Technology of Furfural and reagents Manual By Products, Elsevier Science, 2000; r.xing, a.v. subahmanyam, h.olsay, g.w.huber.process of jet and diesel fuel range from gaseous-derived sources solutions, green chem.2010,12,1933. Therefore, the preparation of the furan alcohol biodiesel by using the biomass-based furfural and the biomass-based acrolein is an important way for reasonably utilizing the biomass-based furfural and the biomass-based acrolein.
Disclosure of Invention
The invention aims to provide a method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein, which has the advantages of small catalyst consumption, high product yield, easy separation, no need of additional hydrogen in the reaction process, low production cost, safety, no hidden danger and environmental friendliness.
The technical scheme of the invention is as follows:
a method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein comprises dissolving furylacrolein in fatty alcohol, adding supported nano metal catalyst, heating to 150-350 deg.C, and reacting to obtain furan alcohol biodiesel; the metal in the supported nano metal catalyst comprises one or more of nickel, iron, cobalt, palladium and ruthenium, and the carrier is nano porous carbon.
Wherein, stirring is carried out during the reaction, and the reaction is carried out for 0.5 to 6 hours under the condition of the stirring rotating speed of 100 to 3000 r/min.
The fatty alcohol is C1-C3 fatty alcohol, and the furyl acrolein is a biomass-based furfural derivative of C7-C8. The dosage ratio of the furyl acrolein to the fatty alcohol can be 0.1 g: 2 mL.
The aliphatic alcohol is methanol, ethanol, 1-propanol, 2-propanol or ethylene glycol; the furyl acrolein is 3- (2-furyl) acrolein or 2-methyl-3- (2-furyl) acrolein.
The loading amount of the metal in the supported nano metal catalyst is 1-30 wt%.
The addition amount of the supported nano metal catalyst is 2-30% of the mass of the furylacrolein. Preferably, the loading amount of the supported nano metal catalyst is 10% of the mass of the furylacrolein.
When the metal in the supported nano metal catalyst comprises one or more of nickel, iron and cobalt, the preparation method is a coordination-reduction method, and the preparation method comprises the following steps:
(1) dissolving nitrate in water or adding EDTA-2Na into the nitrate solution, stirring, and adding NaOH and anhydrous methanol to form a mixed solution;
(2) heating the mixed solution to 200-250 ℃ for reaction, cooling to room temperature, filtering and collecting the precipitate, and drying to obtain powder;
(3) and (3) heating the powder obtained in the step (2) to 400-450 ℃ for thermal reduction treatment to obtain the supported nano metal catalyst.
By the preparation method, in-situ supported catalysts such as Ni @ C, Co @ C, Fe @ C, Fe-Ni @ C, Fe-Co @ C, Ni-Co @ C, Ru doped Ni @ C and Pd doped Ni @ C can be obtained. The in-situ supported catalyst is adopted, so that the condition is mild, the catalytic effect is good, the catalyst is easy to recover and can be repeatedly used; the in-situ supported catalyst can catalyze the in-situ hydrogenation of the furfurylacrolein to prepare the furfuryl alcohol biodiesel with high efficiency and high selectivity, the product is easy to separate, the production cost is low, the technical and economic effects are obvious, and the market application prospect is good.
The metal in the supported nano metal catalyst comprises one or more of palladium and ruthenium, the preparation method is an impregnation method, and the preparation method comprises the following steps:
(1) soaking activated carbon in dilute nitric acid, stirring, washing, and drying under vacuum to obtain activated carbon powder;
(2) adding hydrochloric acid solution of tetrachloropalladate or ruthenium chloride by an isometric immersion method, then ultrasonically dispersing in deionized water, then adding activated carbon powder, stirring, standing, filtering, and vacuumizing to obtain the supported nano metal catalyst.
The invention has the advantages that: the preparation method is simple and easy to operate, safe, good in economic benefit, few in by-products and environment-friendly. The supported nano metal catalyst is adopted, so that the catalyst is low in cost, mild in condition, good in catalytic effect, easy to recover and capable of being repeatedly used; the supported nano metal catalyst can catalyze the furfurylacrolein to prepare the furfuryl alcohol biodiesel with high efficiency and high selectivity, and the product is easy to separate and has low production cost, obvious technical and economic effects and wide market application prospect.
Detailed Description
The present invention is further illustrated by the following specific examples. In the examples, the catalysts such as Ni @ C, Co @ C, Fe @ C and the like are prepared by a coordination-reduction method, the loading of metals such as nickel and the like is 20 wt%, the activation temperature is 425 ℃, and the activation time is 2 hours.
Specifically, the preparation method of Ni @ C comprises the following steps: weighing 20g of nickel nitrate hexahydrate, fully dissolving the nickel nitrate hexahydrate in 80mL of deionized water, adding 13.5g of EDTA-2Na, strongly stirring, adding 1.5g of NaOH and 20mL of anhydrous methanol after a emerald green homogeneous transparent solution is formed, continuously stirring until the solution becomes a lake blue transparent state, transferring the liquid into a stainless steel hydrothermal synthesis kettle, treating for 20 hours at 220 ℃, cooling the hydrothermal kettle to the room temperature, filtering and collecting green precipitates, sequentially washing with water and acetone for several times, and drying the green powder in an oven for 12 hours at 100 ℃. Then the green powder is subjected to thermal reduction treatment for 2h under hydrogen at 425 ℃ in a tube furnace, the heating rate is 5 ℃/min, and the hydrogen flow is 20 mL/min. And finally, waiting for the sample to be fully cooled to room temperature, and obtaining black solid powder as the supported nano metal catalyst Ni @ C.
The preparation method of Co @ C, Fe @ C is the same as that of Ni @ C, and nickel nitrate is replaced by cobalt nitrate and ferric nitrate. In the examples, the preparation method of Fe-Ni @ C, Fe-Co @ C, Ni-Co @ C is the same as that of Ni @ C, and the molar fraction is as follows: 1 adding ferric nitrate and nickel nitrate, ferric nitrate and cobalt nitrate, nickel nitrate and cobalt nitrate.
The preparation method of Ru/C and Pd/C comprises the following steps: firstly, activated carbon was soaked in dilute nitric acid (20 wt%) with stirring, then washed and dried under vacuum at 100 ℃ overnight. And (2) adopting an isometric immersion method, adding tetrachloropalladaic acid or hydrochloric acid solution of ruthenium chloride into a clean beaker, performing ultrasonic dispersion in 20mL of deionized water, adding a proper amount of activated carbon powder, stirring for 2 hours, standing overnight, filtering every other day, washing with deionized water, and performing vacuum drying to obtain the available palladium and ruthenium catalyst.
The preparation method of the Ni-doped Ru/C and the Ni-doped Pd/C comprises the following steps: when the method is an isometric impregnation method, a certain amount of nickel nitrate solution is added according to theoretical loading, and the nickel nitrate solution and the ruthenium-containing solution and the palladium-containing solution are respectively blended and impregnated. The mol ratio of doping is 1: 10-20. In the examples 1: 19.
The preparation method of the Ru-doped Ni @ C and the Pd-doped Ni @ C comprises the following steps: ruthenium salt or palladium-containing solution is used for replacing part of nickel nitrate, and the nickel nitrate is prepared by adopting a coordination-reduction method (the same as the preparation method of Ni @ C). The mol ratio of doping is 1: 10-20. In the examples 1: 19.
Example 1
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, methanol as a solvent and in-situ supported Ni @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: 0.1g of 3- (2-furyl) acrolein is dissolved in 2mL of methanol, 0.01 g of Ni @ C catalyst is added, the reaction is carried out for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and the 3- (2-furyl) propanol is prepared by selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein through the in-situ grown nano nickel taking porous carbon as a carrier. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 78.34%.
Example 2
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, ethanol as a solvent and in-situ supported Ni @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: 0.1g of 3- (2-furyl) acrolein is dissolved in 2mL of ethanol, 0.01 g of Ni @ C catalyst is added, the reaction is carried out for 2 hours at the temperature of 200 ℃ and the stirring speed of 600 r/min, and the 3- (2-furyl) propanol is prepared by selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein through the in-situ grown nano nickel taking porous carbon as a carrier. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 86.12%.
Example 3
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, 1-propanol as a solvent and in-situ supported Ni @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 1-propanol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 rpm, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 80.42%.
Example 4
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and in-situ supported Ni @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 81.42%.
Example 5
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 3- (2-furyl) acrolein as a substrate, the ethylene glycol as a solvent and the in-situ supported Ni @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethylene glycol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 84.22%.
Example 6
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 2-methyl-3- (2-furyl) acrolein as a substrate, methanol as a solvent and in-situ supported Ni @ C as a catalyst to prepare 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of methanol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 78.34%.
Example 7
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 2-methyl-3- (2-furyl) acrolein as a substrate, takes the ethanol as a solvent, and takes the in-situ supported Ni @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 200 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 86.82%.
Example 8
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 2-methyl-3- (2-furyl) acrolein as a substrate, 1-propanol as a solvent and in-situ supported Ni @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 1-propanol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 rpm, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 80.42%.
Example 9
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 2-methyl-3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and in-situ supported Ni @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 89.42%.
Example 10
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 2-methyl-3- (2-furyl) acrolein as a substrate, the ethylene glycol as a solvent and the in-situ supported Ni @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethylene glycol, adding 0.01 g of Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 85.42%.
Example 11
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, methanol as a solvent and in-situ supported Co @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of methanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 78.34%.
Example 12
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, ethanol as a solvent and in-situ supported Co @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 200 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 83.14%.
Example 13
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, 1-propanol as a solvent and in-situ supported Co @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 1-propanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 rpm, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 80.52%.
Example 14
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and in-situ supported Co @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 81.42%.
Example 15
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, ethylene glycol as a solvent and in-situ supported Co @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethylene glycol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 84.22%.
Example 16
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 2-methyl-3- (2-furyl) acrolein as a substrate, methanol as a solvent and in-situ supported Co @ C as a catalyst to prepare 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of methanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ under the condition of stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 78.94%.
Example 17
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 2-methyl-3- (2-furyl) acrolein as a substrate, takes the ethanol as a solvent, and takes the in-situ supported Co @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ under the condition of stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 86.12%.
Example 18
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, 1-propanol as a solvent and in-situ supported Co @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and comprises the following specific steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 1-propanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 rpm, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein through the in-situ grown nano nickel taking porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 80.33%.
Example 19
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 2-methyl-3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and in-situ supported Co @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 87.44%.
Example 20
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 2-methyl-3- (2-furyl) acrolein as a substrate, the ethylene glycol as a solvent and the in-situ supported Co @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethylene glycol, adding 0.01 g of Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 82.22%.
Example 21
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, methanol as a solvent and in-situ supported Fe @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of methanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 78.34%.
Example 22
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, ethanol as a solvent and in-situ supported Fe @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 78.12%.
Example 23
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, 1-propanol as a solvent and in-situ supported Fe @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 1-propanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 rpm, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 80.42%.
Example 24
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and in-situ supported Fe @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 79.42%.
Example 25
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 3- (2-furyl) acrolein as a substrate, the ethylene glycol as a solvent and the in-situ supported Fe @ C as a catalyst to prepare the 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethylene glycol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 80.25%.
Example 26
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 2-methyl-3- (2-furyl) acrolein as a substrate, takes the methanol as a solvent and takes the in-situ supported Fe @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of methanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ under the condition of stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 78.34%.
Example 27
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 2-methyl-3- (2-furyl) acrolein as a substrate, takes the ethanol as a solvent, and takes the in-situ supported Fe @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 220 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 76.12%.
Example 28
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, 1-propanol as a solvent and in-situ supported Fe @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and comprises the following specific steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 1-propanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 rpm, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein through the in-situ grown nano nickel taking porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 80.42%.
Example 29
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and in-situ supported Fe @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 79.42%.
Example 30
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes the 2-methyl-3- (2-furyl) acrolein as a substrate, the ethylene glycol as a solvent and the in-situ supported Fe @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethylene glycol, adding 0.01 g of Fe @ C catalyst, reacting for 2 hours at the temperature of 280 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using the nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 86.22%.
Example 31
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and supported Ru/C as a catalyst to prepare the 3- (2-furyl) propanol, and comprises the following specific steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Ru/C catalyst, reacting for 2 hours at the temperature of 220 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 77.63%.
Example 32
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and supported Pd/C as a catalyst to prepare the 3- (2-furyl) propanol, and comprises the following specific steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Pd/C catalyst, reacting for 2 hours at the temperature of 220 ℃ and the stirring speed of 600 r/min, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 74.95%.
Example 33
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and Ru/C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Ru/C catalyst, reacting for 2 hours at 220 ℃ under the condition of stirring rotation speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 89.38%.
Example 34
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, 2-propanol as a solvent and Pd/C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and comprises the following specific steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of 2-propanol, adding 0.01 g of Pd/C catalyst, reacting for 2 hours at 220 ℃ under the condition of stirring rotation speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 84.95%.
Example 35
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, ethanol as a solvent and Ni-doped Ru/C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Ni-doped Ru/C catalyst, reacting for 2 hours at 220 ℃ under the condition of stirring rotation speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 79.48%.
Example 36
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, ethanol as a solvent and Ni-doped Pd/C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Ni-doped Pd/C catalyst, reacting for 2 hours at 220 ℃ under the condition of stirring rotation speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 87.55%.
Example 37
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, ethanol as a solvent and Ru-doped Ni @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Ru-doped Ni @ C catalyst, reacting for 2 hours at 220 ℃ under the condition of stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 89.91%.
Example 38
The method for preparing the furan alcohol biodiesel by in-situ hydrogenation of the furylacrolein, which is provided by the embodiment, takes 2-methyl-3- (2-furyl) acrolein as a substrate, ethanol as a solvent and Pd-doped Ni @ C as a catalyst to prepare the 2-methyl-3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 2-methyl-3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Pd-doped Ni @ C catalyst, reacting for 2 hours at 220 ℃ under the condition of stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 2-methyl-3- (2-furyl) acrolein by using nano nickel grown in situ by using porous carbon as a carrier to prepare the 2-methyl-3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 2-methyl-3- (2-furyl) acrolein was 99.9%, and the selectivity of 2-methyl-3- (2-furyl) -1-propanol was 86.18%.
Example 39
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, methanol as a solvent and in-situ supported Fe-Ni @ C as a catalyst to prepare 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of ethanol, adding 0.01 g of Fe-Ni @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 78.96%.
Example 40
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, ethanol as a solvent and in-situ supported Fe-Co @ C as a catalyst to prepare 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of methanol, adding 0.01 g of Fe-Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 80.11%.
EXAMPLE 41
The method for preparing furan alcohol biodiesel by in-situ hydrogenation of furylacrolein provided by the embodiment takes 3- (2-furyl) acrolein as a substrate, ethanol as a solvent and in-situ supported Ni-Co @ C as a catalyst to prepare 3- (2-furyl) propanol, and the specific method comprises the following steps: dissolving 0.1g of 3- (2-furyl) acrolein in 2mL of methanol, adding 0.01 g of Ni-Co @ C catalyst, reacting for 2 hours at the temperature of 240 ℃ and the stirring speed of 600 revolutions per minute, and selectively catalyzing the in-situ hydrogenation of the 3- (2-furyl) acrolein by using nano nickel which grows in situ and takes porous carbon as a carrier to prepare the 3- (2-furyl) propanol. Analyzing the reaction result by using a gas-mass spectrometer and gas chromatography; the conversion of 3- (2-furyl) acrolein was 99.9%, and the selectivity of 3- (2-furyl) -1-propanol was 82.41%.
The above examples show that: by adopting the method provided by the invention, the furan-based acrolein can be hydrogenated in situ to prepare the furan alcohol biodiesel with high conversion rate and high selectivity; the catalyst has the advantages of cheap and easily obtained raw materials, stable structure, easy regeneration, mild reaction conditions, no need of additional hydrogen, simple and safe reaction process, capability of meeting the requirements of technical economy and wide market application prospect.
Claims (7)
1. A method for preparing furan alcohol biodiesel by in-situ hydrogenation of furan acrolein is characterized in that the furan acrolein is dissolved in fatty alcohol, a supported nano metal catalyst is added, and the furan alcohol biodiesel is obtained after the reaction after the heating to 150-350 ℃; the metal in the supported nano metal catalyst comprises one or more of nickel, iron, cobalt, palladium and ruthenium, and the carrier is nano porous carbon.
2. The method for preparing the furan alcohol biodiesel by the in-situ hydrogenation of the furylacrolein according to the claim 1, wherein the fatty alcohol is C1-C3 fatty alcohol, and the furylacrolein is a biomass-based furfural derivative of C7-C8.
3. The method for preparing the furan alcohol biodiesel by the in-situ hydrogenation of the furan acrolein according to the claims 1-2, wherein the aliphatic alcohol is methanol, ethanol, 1-propanol, 2-propanol or ethylene glycol; the furyl acrolein is 3- (2-furyl) acrolein or 2-methyl-3- (2-furyl) acrolein.
4. The method for preparing the furan alcohol biodiesel by the in-situ hydrogenation of the furylacrolein according to claim 1, wherein the loading amount of the metal in the supported nano metal catalyst is 1-30 wt%.
5. The method for preparing the furan alcohol biodiesel by the in-situ hydrogenation of the furylacrolein according to the claim 4, wherein the loading amount of the supported nano metal catalyst is 2-30% of the mass of the furylacrolein.
6. The method for preparing the furan alcohol biodiesel by the in-situ hydrogenation of the furylacrolein according to claim 1, wherein when the metal in the supported nano metal catalyst comprises one or more of nickel, iron and cobalt, the preparation method is a coordination-reduction method, and the preparation method comprises the following steps:
(1) dissolving nitrate in water or adding EDTA-2Na into the nitrate solution, stirring, and adding NaOH and anhydrous methanol to form a mixed solution;
(2) heating the mixed solution to 200-250 ℃ for reaction, cooling to room temperature, filtering and collecting the precipitate, and drying to obtain powder;
(3) and (3) heating the powder obtained in the step (2) to 400-450 ℃ for thermal reduction treatment to obtain the supported nano metal catalyst.
7. The method for preparing the furan alcohol biodiesel through in-situ hydrogenation of the furylacrolein according to claim 1, wherein the metal in the supported nano metal catalyst comprises one or more of palladium and ruthenium, the preparation method is an impregnation method, and the preparation method comprises the following steps:
(1) soaking activated carbon in dilute nitric acid, stirring, washing, and drying under vacuum to obtain activated carbon powder;
(2) adding hydrochloric acid solution of tetrachloropalladate or ruthenium chloride by an isometric immersion method, then ultrasonically dispersing in deionized water, then adding activated carbon powder, stirring, standing, filtering, washing, and drying in vacuum to obtain the supported nano metal catalyst.
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