CN112657485A - Method for preparing tetrahydrofurfuryl alcohol and pentanediol by furfuryl alcohol hydrogenation - Google Patents
Method for preparing tetrahydrofurfuryl alcohol and pentanediol by furfuryl alcohol hydrogenation Download PDFInfo
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- furfuryl alcohol
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Abstract
The invention discloses a method for preparing tetrahydrofurfuryl alcohol and pentanediol by furfuryl alcohol hydrogenation. The method comprises the steps of taking furfuryl alcohol as a substrate, isopropanol as a solvent, and a metal-supported carbon-based catalyst and calcium oxide as a combined catalyst, and carrying out hydrogenation reaction under the condition of stirring at 150-180 ℃ in a hydrogen environment of 1-4 MPa to prepare tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol. The method realizes high-value furfuryl alcohol conversion, has simple and convenient production process and low operation difficulty, and has certain popularization and application prospect.
Description
Technical Field
The invention belongs to the technical field of synthesis of biomass-based high-grade chemicals, and particularly relates to a method for preparing tetrahydrofurfuryl alcohol and pentanediol by furfuryl alcohol hydrogenation.
Background
With the use of fossil resources in large quantities, the problems of energy shortage and environmental pollution become increasingly significant, and the search for a high-efficiency and environment-friendly alternative resource has become a current research hotspot. Biomass has the remarkable characteristics of being renewable, large in reserve, wide in distribution and the like, and is the only renewable resource capable of being used for synthesizing chemicals, so that the biomass draws wide attention of researchers. Furfuryl alcohol is an important platform compound obtained by catalytic conversion of biomass, and is widely applied to industries such as medicine and chemical industry. Based on active carbon-carbon double bonds and hydroxyl groups in the furfuryl alcohol structure, high-value products such as tetrahydrofurfuryl alcohol, 1, 2-pentanediol, 1, 5-pentanediol and the like can be further obtained by adopting a catalytic hydro-conversion mode. Wherein, the 1, 2-pentanediol is used as an important fine chemical intermediate and is an important raw material for synthesizing the bactericide propiconazole. Meanwhile, it has been widely used in sunscreen cream and infant care products because it can dissolve poorly soluble active ingredients. The 1, 5-pentanediol is mainly used for producing polyester resin, polyester polyol, polyurethane foam plastics and the like, and the tetrahydrofurfuryl alcohol can be used for preparing succinic acid, pentanediol, tetrahydrofuran, pyran and the like, and also can be used as a solvent of coating, resin and grease, and a raw material for organic synthesis of plasticizer, herbicide, insecticide and the like.
CN108911949A discloses a method for preparing 1, 2-pentanediol by catalyzing furfuryl alcohol hydrogenation by using a copper-based catalyst, wherein under the action of a zinc oxide-loaded copper-based catalyst, the selectivity of 1, 2-pentanediol alcohol can reach about 70%. CN106732602A discloses a method for preparing a compound with MgmConAlyOxThe method for preparing pentanediol by catalyzing furfural with Pt-based supported catalyst serving as carrier has the furfural conversion rate close to 94.6% and the selectivity of 1, 5-pentanediol and 1, 2-pentanediol of 22.6% and 33.9 respectively under the optimal condition% of the total weight of the composition. CN106622219A discloses a furfuryl alcohol in gamma-Al2O3The method for preparing tetrahydrofurfuryl alcohol by hydrogenation under the action of the loaded Ru catalyst has the tetrahydrofurfuryl alcohol selectivity of over 95 percent. At present, the research reports of a catalytic reaction system for coproducing tetrahydrofurfuryl alcohol and pentanediol by taking furfuryl alcohol as a raw material are few, and the catalytic reaction system has important research significance for the catalytic reaction system with high efficiency, easy regulation and low cost.
Disclosure of Invention
The invention aims to provide a method for preparing tetrahydrofurfuryl alcohol and pentanediol by furfuryl alcohol hydrogenation, which takes a carbon-based catalyst and calcium oxide as a combined catalyst and isopropanol as a solvent to catalyze furfuryl alcohol hydrogenation to coproduce tetrahydrofurfuryl alcohol and pentanediol in a hydrogen atmosphere, and completes the high-target selectivity preparation of tetrahydrofurfuryl alcohol and pentanediol on the basis of the prior art.
The invention discloses a method for preparing tetrahydrofurfuryl alcohol and pentanediol by furfuryl alcohol hydrogenation, which comprises the following steps:
the method comprises the steps of taking furfuryl alcohol as a substrate, isopropanol as a solvent, and a metal-supported carbon-based catalyst and calcium oxide as a combined catalyst, and carrying out hydrogenation reaction under the condition of stirring at 150-180 ℃ in a hydrogen environment of 1-4 MPa to prepare tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol.
Preferably, the furfuryl alcohol concentration is 0.1-1 mol/L, the mass ratio of the metal-supported carbon-based catalyst to the furfuryl alcohol is 0.1-1: 1, and the mass ratio of the calcium oxide to the furfuryl alcohol is 0.8-1.2: 1.
Preferably, the metal supported carbon-based catalyst is Pt/C with Pt loading of 5-10% or Pd/C with Pd loading of 3-10%.
Preferably, the stirring speed is 500-1000 rpm.
Preferably, the reaction time is 2-10 h.
The invention has the beneficial effects that:
according to the invention, the preparation of tetrahydrofurfuryl alcohol and pentanediol through furfuryl alcohol selective hydrogenation conversion is realized by adopting a mode of combining calcium oxide and a carbon-based catalyst and regulating and controlling alkaline sites and active metal centers required by a reaction system. Under the reaction system of the invention, the conversion rate of the raw materials is close to 100%, and the selectivity of the tetrahydrofurfuryl alcohol and the pentanediol is up to more than 85%.
In a word, the method has the advantages of feasible technical scheme, simple and convenient production process, low operation difficulty and certain popularization and application prospect.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof.
The metal-supported carbon-based catalysts used in the following examples were prepared by the following method:
Pt/C with 10% Pt loading: firstly, preparing chloroplatinic acid aqueous solution with the Pt content of 10mg/mL, putting 20mL of the chloroplatinic acid aqueous solution into a 50mL round-bottom flask, adding 2g of activated carbon carrier, stirring at room temperature for 6h, then putting the solution into a drying oven for drying at 105 ℃, then reducing the dried sample in mixed gas of 60% hydrogen and 40% nitrogen at 300 ℃ for 3h, and putting the reduced catalyst into a dryer for storage and standby application.
Pt/C with 5% Pt loading: the preparation process of the catalyst is similar to the preparation method of the Pt/C with the Pt loading of 10%, the dosage of the chloroplatinic acid aqueous solution is adjusted to be 10mL, and other experimental steps are kept consistent.
Pd/C with 3% Pd loading: firstly, dissolving and diluting palladium chloride by using 1mol/L hydrochloric acid to prepare a palladium chloride aqueous solution with the Pd content of 10mg/mL, putting 3mL of the palladium chloride aqueous solution into a 50mL round-bottom flask, adding 1g of activated carbon carrier, stirring at room temperature for 6 hours, then putting into an oven for drying at 105 ℃, then reducing the dried sample in a mixed gas of 60% hydrogen and 40% nitrogen at 300 ℃ for 3 hours, and putting the reduced catalyst into a dryer for storage and standby.
Pd/C with 5% Pd loading: the preparation process of the catalyst is similar to the preparation method of the Pd/C with the Pd loading of 3%, the dosage of the palladium chloride aqueous solution is adjusted to be 5mL, and other experimental steps are kept consistent.
Pd/C with 10% Pd loading: the preparation process of the catalyst is similar to the preparation method of the Pd/C with the Pd loading of 3%, the dosage of the palladium chloride aqueous solution is adjusted to 10mL, and other experimental steps are kept consistent.
Example 1
15mL of isopropanol serving as a solvent, 0.1mol/L of furfuryl alcohol serving as a substrate, 4MPa of hydrogen pressure, 500rpm of stirring speed, 10% Pt/C of Pt loading amount serving as a carbon-based catalyst, 1:1 mass ratio of Pt/C to furfuryl alcohol, 0.8:1 mass ratio of calcium oxide to furfuryl alcohol, 180 ℃ of reaction temperature and 6 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental result shows that under the reaction conditions, the conversion rate of furfuryl alcohol is 100%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 36.7%, 36.1% and 21.5%, respectively.
Example 2
15mL of isopropanol serving as a solvent, 1mol/L of furfuryl alcohol serving as a substrate, 4MPa of hydrogen pressure, 1000rpm of stirring speed, 10% Pt/C of Pt loading capacity serving as a carbon-based catalyst, 1:1 mass ratio of the Pt/C to the furfuryl alcohol, 1.2:1 mass ratio of calcium oxide to the furfuryl alcohol, 180 ℃ of reaction temperature and 10 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental result shows that under the reaction conditions, the conversion rate of furfuryl alcohol is 100%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 58.9%, 7.6% and 5.4%, respectively.
Example 3
20mL of isopropanol serving as a solvent, 0.3mol/L of furfuryl alcohol serving as a substrate, 2MPa of hydrogen pressure, 600rpm of stirring speed, 3% Pd/C of Pd loading capacity serving as a carbon-based catalyst, 0.1:1 mass ratio of Pd/C to furfuryl alcohol, 0.8:1 mass ratio of calcium oxide to furfuryl alcohol, 180 ℃ of reaction temperature and 6 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental results show that under the above reaction conditions, the conversion rate of furfuryl alcohol is 85.0%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 32.1%, 35.3% and 16.0%, respectively.
Example 4
20mL of isopropanol serving as a solvent, 0.3mol/L of furfuryl alcohol serving as a substrate, 1MPa of hydrogen pressure, 800rpm of stirring speed, 3% Pd/C of Pd loading capacity serving as a carbon-based catalyst, 0.1:1 mass ratio of Pd/C to furfuryl alcohol, 0.8:1 mass ratio of calcium oxide to furfuryl alcohol, 150 ℃ of reaction temperature and 2 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental results show that under the above reaction conditions, the conversion rate of furfuryl alcohol is 39.4%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 40.6%, 32.7% and 5.4%, respectively.
Example 5
25mL of isopropanol serving as a solvent, 0.5mol/L of furfuryl alcohol serving as a substrate, 4MPa of hydrogen pressure, 500rpm of stirring speed, 5% Pd/C of Pd loading capacity serving as a carbon-based catalyst, 0.7:1 of the mass ratio of Pd/C to furfuryl alcohol, 1.2:1 of the mass ratio of calcium oxide to furfuryl alcohol, 160 ℃ of reaction temperature and 4 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental results show that under the above reaction conditions, the conversion rate of furfuryl alcohol is 70.5%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 39%, 18% and 14%, respectively.
Example 6
20mL of isopropanol serving as a solvent, 0.5mol/L of furfuryl alcohol serving as a substrate, 4MPa of hydrogen pressure, 600rpm of stirring speed, 5% Pt/C of Pt loading amount serving as a carbon-based catalyst, 0.8:1 of Pt/C to furfuryl alcohol mass ratio, 1.2:1 of calcium oxide to furfuryl alcohol mass ratio, 170 ℃ of reaction temperature and 10 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental results show that under the above reaction conditions, the conversion rate of furfuryl alcohol is 89.4%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 43.3%, 30.1% and 20.4%, respectively.
Example 7
15mL of isopropanol serving as a solvent, 0.1mol/L of furfuryl alcohol serving as a substrate, 4MPa of hydrogen pressure, 1000rpm of stirring speed, 10% Pd/C of Pd loading capacity serving as a carbon-based catalyst, 0.6:1 of mass ratio of Pd/C to furfuryl alcohol, 1.2:1 of mass ratio of calcium oxide to furfuryl alcohol, 150 ℃ of reaction temperature and 8 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental results show that under the above reaction conditions, the conversion rate of furfuryl alcohol is 81.8%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 38.9%, 36.8% and 15.4%, respectively.
Example 8
25mL of isopropanol serving as a solvent, 0.8mol/L of furfuryl alcohol serving as a substrate, 4MPa of hydrogen pressure, 600rpm of stirring speed, 5% Pt/C of Pt loading amount serving as a carbon-based catalyst, 0.4:1 of Pt/C to furfuryl alcohol mass ratio, 1.0:1 of calcium oxide to furfuryl alcohol mass ratio, 180 ℃ of reaction temperature and 7 hours of reaction time. And filtering a product after reaction by using a 0.22-micron organic filter membrane, and detecting the conversion rate of the raw material and the yield of the product by using Agilent 7890A. The experimental results show that under the above reaction conditions, the conversion rate of furfuryl alcohol is 83.9%, and the selectivity of tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol is 35.1%, 55.2% and 10.4%, respectively.
Claims (5)
1. A method for preparing tetrahydrofurfuryl alcohol and pentanediol by furfuryl alcohol hydrogenation is characterized by comprising the following steps:
the method comprises the steps of taking furfuryl alcohol as a substrate, isopropanol as a solvent, and a metal-supported carbon-based catalyst and calcium oxide as a combined catalyst, and carrying out hydrogenation reaction under the condition of stirring at 150-180 ℃ in a hydrogen environment of 1-4 MPa to prepare tetrahydrofurfuryl alcohol, 1, 2-pentanediol and 1, 5-pentanediol.
2. The method according to claim 1, wherein the furfuryl alcohol concentration is 0.1 to 1mol/L, the mass ratio of the metal supported carbon-based catalyst to furfuryl alcohol is 0.1 to 1:1, and the mass ratio of calcium oxide to furfuryl alcohol is 0.8 to 1.2: 1.
3. The method of claim 1, wherein the metal-supported carbon-based catalyst is Pt/C with a Pt loading of 5% to 10% or Pd/C with a Pd loading of 3% to 10%.
4. The method of claim 1, wherein the stirring is at a rate of 500 to 1000 rpm.
5. The method according to claim 1, wherein the reaction time is 2 to 10 hours.
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