CN115636720A - Method for producing 1, 2-propylene glycol by one-step method catalysis biomass - Google Patents
Method for producing 1, 2-propylene glycol by one-step method catalysis biomass Download PDFInfo
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Abstract
The invention discloses a method for producing 1, 2-propylene glycol by catalyzing biomass through a one-step method, and belongs to the field of environmental chemical industry. The method comprises the following specific steps: adding a catalyst and biomass (sucrose) into a reactor at the same time, adding the catalyst and the biomass (sucrose) according to the proportion of 100-200 mg of biomass, 10-20 mL of water and 50-300 mg of the catalyst, and carrying out hydrogenation catalytic reaction at the reaction temperature of 180-240 ℃ for 30-240 min. The raw materials of the invention mainly come from biomass of common products in chemical production, the cost is low, the cost is reduced, the process is simple and clear, the operation is convenient, no secondary pollution is caused, the demand on fossil energy is reduced, and certain economic and social benefits are achieved.
Description
Technical Field
The invention relates to a method for producing 1, 2-propylene glycol by catalyzing biomass by a one-step method, in particular to a hydrogenation catalysis method taking a core-shell structure as a catalyst, belonging to the field of environmental chemical industry.
Background
Biomass is a renewable resource with wide distribution and low price, and has been widely studied in the fields of resource utilization and energy regeneration for many years. 1, 2-propylene glycol is an important high value-added chemical, and currently, the industrial production of 1, 2-propylene glycol mainly takes fossil fuel as a raw material, and the method mainly adopts a propylene oxide direct hydration method, a propylene oxide indirect hydration method, a propylene direct catalytic oxidation method, a weak base hydrolysis method and an esterification method which take 1, 2-dichloropropane as a raw material, and the like. However, due to the deepening of the crisis of fossil resources and the current situation that global climate is continuously deteriorated by global fossil fuel-based industries, it is urgent to replace fossil fuel with a renewable material that is green, sustainable, and environmentally friendly. The reaction way of directly taking biomass such as glucose and the like as raw materials for catalytic conversion into the propylene glycol is proved to be feasible, and the method has the characteristics of simple process, rapidness, high efficiency, environmental protection and the like, and has wide development prospect. The sucrose resource is very abundant, widely exists in plants, and is an ideal raw material for biomass resource.
Beta molecular sieves have begun to be used extensively in biomass reaction system research in recent years. At present, the modification method aiming at the Beta molecular sieve is mainly divided into three types, namely: dealuminization modification, desilication modification and metal modification, wherein the dealuminization modification and the metal modification are most widely applied. In most experiments, dealumination modification and desilication modification are often carried out together with metal modification to construct a molecular sieve catalytic system containing metal nanoparticles, and the catalytic capability of the catalytic system is influenced by adjusting the pore size, the pore volume, the specific surface area and the distribution of acid sites.
Disclosure of Invention
The invention aims to provide a method for converting biomass into high-added-value propylene glycol by using biomass such as sucrose as a raw material and under the action of a catalyst.
The invention provides a method for producing 1, 2-propylene glycol by catalyzing biomass, which takes a core-shell structure Beta molecular sieve catalyst as a catalyst and biomass as a raw material, wherein the core-shell structure Beta molecular sieve catalyst is obtained by subjecting a Beta molecular sieve to dealuminization treatment, pt impregnation and Mg (OH) 2 And (3) obtaining the modified product.
In one embodiment of the invention, the biomass is cellulose, hemicellulose, lignin, corncob, corn stover or sucrose, preferably sucrose.
In one embodiment of the invention, the method comprises: adding a catalyst and biomass into a reactor according to the proportion of 100-200 mg of biomass, 10-20 mL of water and 50-300 mg of catalyst, and introducing H 2 Air is exhausted and then 5 to 6MPa of H is introduced 2 The hydrogenation catalytic reaction is carried out under the conditions that the reaction temperature is 180-240 ℃ and the reaction time is 30-240 min.
In one embodiment of the invention, the preparation method of the core-shell structure Beta molecular sieve catalyst comprises the following steps:
(1) Mixing a Beta molecular sieve with concentrated nitric acid, performing condensation reflux to perform dealumination, washing and drying to obtain a dealuminated and modified Beta molecular sieve deAl-Beta;
(2) Impregnating the dealuminized and modified Beta molecular sieve obtained in the step (1) with a chloroplatinic acid solution, standing for aging, drying, roasting at high temperature, mixing the roasted catalyst with water, adding the mixture into a reaction kettle, and carrying out PtO on the catalyst in a high-pressure hydrogen environment 2 Reducing the Pt to obtain a Pt modified catalyst Pt/deAl-Beta of metal Pt;
(3) Mixing the catalyst Pt/deAl-Beta obtained in the step (2), mgO and water, carrying out hydrothermal reaction in a high-pressure hydrogen environment, carrying out solid-liquid separation, drying, grinding into powder, and then carrying out high-temperature roasting to obtain the core-shell structure Beta molecular sieve catalyst Pt/deAl-Beta @ Mg (OH) 2 。
In one embodiment of the invention, in the step (1), the ratio of the Beta molecular sieve to the concentrated nitric acid is 1g:20mL, and carrying out dealumination for 10-20h by condensation and reflux.
In one embodiment of the present invention, in step (2), the amount of catalyst-supported Pt is 1 to 10wt%.
In one embodiment of the invention, in the step (2), the high-temperature roasting is carried out at 450 ℃ for 4h, and preferably, the heating rate is 2 ℃/min; wherein the high-temperature roasting is performed in a static air atmosphere.
In one embodiment of the present invention, in the step (2), the reduction is performed by hydrothermal reaction under the conditions of 5MPa hydrogen pressure and 200 ℃ for 4h.
In one embodiment of the invention, in step (3), mgO is added in an amount of 2.5 to 12.5wt%, preferably 5wt%, based on the mass of the catalyst Pt/deAl-Beta.
In one embodiment of the present invention, in the step (3), the hydrothermal reaction is performed under 5MPa of hydrogen pressure, 200 ℃ and 600r/min for 4h.
In one embodiment of the present invention, in the step (3), the high-temperature calcination refers to calcination at 550 ℃ for 6 hours, preferably, calcination in a flowing air atmosphere.
In an embodiment of the invention, the preparation method of the core-shell structure Beta molecular sieve catalyst specifically comprises the following steps:
step 1: commercial grade Beta molecular sieve was mixed with concentrated nitric acid at a ratio of 1g:20mL of the solution is added into a three-neck round-bottom flask, and a stirrer is added after the mixture is uniformly mixed. The round bottom flask was placed in an oil bath at a controlled temperature of 80 ℃ and was subjected to condensation reflux dealumination at a stirring rate of 200rpm for 20h. And (3) centrifuging the solid-liquid mixture after dealumination by a high-speed centrifuge at the rotating speed of 3000rpm for 20min. And washing away the nitric acid remained on the Beta molecular sieve by using deionized water, wherein the method comprises the steps of adding a solid component and enough deionized water into a centrifugal tube, strongly shaking to ensure that the molecular sieve is uniformly mixed in the deionized water again, and centrifuging. The above steps are repeated until the supernatant pH after centrifugation is neutral. The washed solid components were dried in an oven set at 150 ℃. The solid powder obtained at this time is the dealuminized and modified Beta molecular sieve which is marked as deAl-Beta.
And 2, step: dipping a chloroplatinic acid solution by using an isometric dipping method, wherein dipping is carried out according to the loading amount of Pt of 1-10 wt%, then, standing and aging a sample in air at normal temperature for 6h, drying at 105 ℃ for 6h, and finally roasting in a tube furnace at 450 ℃ in the atmosphere of static air for 4h, wherein the heating rate is 2 ℃/min. Adding a certain amount of catalyst and water into a reaction kettle, carrying out hydrothermal treatment for 4h under the conditions of 5MPa of hydrogen pressure and 200 ℃, and carrying out PtO on the catalyst 2 Is reduced to Pt. Thus, the preparation of the metal modified dealuminized Beta (deAl-Beta) molecular sieve is completed and is marked as Pt/deAl-Beta.
And 3, step 3: adding 50-300 mg of catalyst, 2.5-12.5 wt% of MgO, 10mL of deionized water and a magnetic stirrer into a reactor, exhausting for 3 times by using 5MPa hydrogen as the reactor, and carrying out hydrothermal reaction for 4 hours at 200 ℃ and 600 r/min. And after the reaction is finished, naturally cooling to room temperature. The solid-liquid mixture was then separated by a high speed centrifuge (4000rpm, 4min), and the centrifuged solid was dried in an oven at a temperature of 150 ℃ overnight. Then placing the mixture in an agate mortar, grinding the mixture for 30min after uniform mixing, transferring the fully ground solid powder into a crucible, and placing the crucible in a tubular furnace to roast the powder for 6h under flowing air at 550 ℃ so as to remove impurities. To this end, the preparation of the metal-modified dealuminated Beta molecular sieves was completed and was noted as Pt/deAl-Beta @ Mg (OH) 2 。
The beneficial effects of the invention are:
(1) The invention designs a core-shell structure catalyst, a core-shell structure is formed by Beta molecular sieves obtained by dealumination treatment, metal impregnation and alkali modification, the core-shell structure catalyst can be used for catalyzing biomass to produce 1, 2-propylene glycol by a one-step method, the reusability is good, and the cost is controllable.
(2) The raw materials of the invention mainly come from biomass of common products in chemical production, the cost is low, and the cost is reduced.
(3) The method can be completed through one-step reaction, and has simple process and convenient operation.
(4) The reaction temperature condition of the invention is relatively mild, the supercritical state is not reached, the reaction rate is fast, and the treatment efficiency is high.
Drawings
Fig. 1 is an XRD analysis pattern of the material of the modification process when the catalyst of example 1 is prepared.
Figure 2 is an analysis of the effect of different Pt loadings on sucrose catalytic efficiency in example 2.
FIG. 3 is a graph showing the effect of different catalyst amounts on the yield of propylene glycol from sucrose in example 3.
FIG. 4 is Pt/deAl-beta @ Mg (OH) of example 5 2 And (4) analyzing the reusability of the catalytic reaction.
Detailed Description
To further illustrate the technical means and effects of the present invention, the following detailed description is given with reference to the accompanying drawings and specific embodiments.
In the present invention, the biomass is sucrose produced by general industrial production.
Commercial grade Beta molecular sieves were purchased from southern university catalyst factories.
EXAMPLE 1 preparation of the catalyst
Step 1: commercial grade Beta molecular sieve and concentrated nitric acid (GR, 65-68%) were mixed at 1g:20mL of the solution is added into a three-neck round-bottom flask, and a stirrer is added after the mixture is uniformly mixed. Putting the round-bottom flask into an oil bath, controlling the temperature at 80 ℃, and carrying out condensation reflux dealumination for 10-20h at the stirring speed of 200 rpm. And centrifuging the solid-liquid mixture after dealuminization by a high-speed centrifuge at the rotating speed of 3000rpm for 20min. And washing away the nitric acid remained on the Beta molecular sieve by using deionized water, wherein the method comprises the steps of adding a solid component and sufficient deionized water into a centrifugal tube, strongly shaking to ensure that the molecular sieve is uniformly mixed in the deionized water again, and centrifuging. The above steps were repeated until the supernatant pH after centrifugation became neutral. The washed solid components were dried in an oven set at 150 ℃. The solid powder obtained at this time is the dealuminized and modified Beta molecular sieve which is marked as deAl-Beta.
Step 2: and (3) adding the solid powder into a chloroplatinic acid solution by using an isometric impregnation method, uniformly stirring, wherein impregnation is carried out according to the loading of Pt in the catalyst of 3wt%, and carrying out ultrasonic treatment for 15min. Then, the sample was left to stand and age in air at normal temperature for 6 hours and dried at 105 ℃ for 6 hours, finally in a tube furnace under an atmosphere of static air，Roasting at 450 deg.c for 4 hr at heating rate of 2 deg.c/min. Adding a certain amount of calcined catalyst and water into a reaction kettleHydrothermal treatment at 200 deg.C under 5MPa hydrogen pressure for 4h, ptO on catalyst 2 Is reduced to Pt. Thus, the preparation of the metal modified dealuminized Beta (deAl-Beta) molecular sieve is completed and is marked as Pt/deAl-Beta.
And step 3: 150mg of catalyst, 5wt% of MgO, 10mL of deionized water and a magnetic stirrer are added into a reactor, 5MPa of hydrogen is used for exhausting the gas for 3 times, and then 5M Pa of H is added 2 And carrying out hydrothermal reaction for 4h at 200 ℃ and 600 r/min. And after the reaction is finished, naturally cooling to room temperature. The solid-liquid mixture was then separated by a high speed centrifuge (4000rpm, 4min), and the centrifuged solid was dried in an oven at a temperature of 150 ℃ overnight. Then placing the mixture in an agate mortar, grinding the mixture for 30min after uniform mixing, transferring the fully ground solid powder into a crucible, and placing the crucible in a tubular furnace to roast for 6h under flowing air at 550 ℃ to remove impurities. To this end, the preparation of the metal-modified dealuminated Beta molecular sieves was completed and was noted as Pt/deAl-Beta @ Mg (OH) 2 。
And 4, step 4: adding a certain amount of biomass into the reaction system, and sealing the reaction kettle again. Reacting for a certain time at a certain temperature, cooling, and respectively collecting a liquid-phase product and a solid-phase catalyst. The liquid phase product is quantitatively analyzed by using a gas chromatograph (Agilent 7820A) with a FID detector, the solid catalyst is characterized, and the solid catalyst is stored after being cleaned so as to be convenient for next use.
FIG. 1 shows Beta molecular sieves, deAl-Beta, pt/deAl-Beta and Pt/deAl-Beta @ Mg (OH) 2 According to an XRD pattern of the catalyst, diffraction peaks of Pt are completely matched with Pt (111), (200) and (220) crystal faces in JCPDS library 70-2057, which shows that after the dealumination modification by concentrated nitric acid, the metal loading by high-temperature calcination and the alkali modification treatment, severe framework collapse of the Beta molecular sieve does not occur, and Pt is successfully loaded on the catalyst. Mg (OH) 2 After loading, the half-peak widths of Pt (111) and Pt (200) in the catalyst are increased, which shows that the Mg (OH) 2 shell increases the dispersity of Pt nanoparticles under the hydrothermal condition and effectively inhibits the agglomeration of the Pt nanoparticles. No Mg (OH) appears in the XRD pattern 2 The peak of (3) indicates Mg (OH) 2 Covering the surface of the molecular sieve in an amorphous mode.
Example 2
10mL of an aqueous sucrose solution (11.25 mg/mL) and 200mg of a catalyst were charged into a reactor at a reaction temperature of 200 ℃ under a reaction of H 2 The initial pressure is 6MPa, the reaction is carried out for 3h, the propylene glycol is obtained by separating the product, wherein the rest operation steps and parameters in the preparation process of the catalyst are the same as those in example 1, and the influence on the catalytic hydrogenation reaction when the loading of Pt is respectively 0%, 1%, 3%, 5% and 7% for impregnation is examined.
The results are shown in FIG. 2 and indicate that the yields for propylene glycol were 4.12%, 26.94%, 33.48%, 32.62% and 31.22% in this order. Wherein, the Pt loaded alone can inhibit the conversion of the propylene glycol, and Mg (OH) is introduced 2 The yield of propylene glycol was then increased by 29.52%. The optimum loading of Pt was thus set to 3wt%.
Example 3
10mL of sucrose aqueous solution (11.25 mg/mL) and 200mg of catalyst were added to the reactor, the remaining operation steps and parameters were the same as in example 1, and the influence of the catalyst obtained when the amount of MgO added ranged from 0% to 80% by weight on the catalytic hydrogenation reaction was examined.
The results show that the propylene glycol yield is 20-34% when the addition amount of MgO is 2.5-12.5 wt%. Wherein, the catalyst prepared by adding 5 percent of MgO by mass fraction has the best propylene glycol yield of 33.5 percent.
The mass fraction of MgO is selected to be 5%, the adding amount of the catalyst is replaced, and 50mg, 100mg, 150mg, 200mg, 250mg and 300mg are respectively added into a reaction system, and the rest is the same as above.
The results are shown in fig. 3, which shows that the propylene glycol yield is gradually increased with the increase of the catalyst amount, and the yield is 33.48% when the catalyst amount is 200mg, and 32.1% when the catalyst amount is 250mg, and the subsequent increase of the catalyst amount cannot continue to improve the propylene glycol yield. In addition, the conversion rate of sucrose was kept to 95% or more.
Example 4
10mL of an aqueous sucrose solution (11.25 mg/mL) and 200mg of 3Pt/deAl-beta @5Mg (OH) 2 The catalyst (example 1) was added to the reactor,H 2 the initial pressure is 6MPa, the reaction time is 60-240 min at 180-240 ℃, the optimal reaction temperature is 190-210 ℃, and the reaction time is 150-200 min.
Example 5
The solid catalyst in the reactor was removed, rinsed with excess deionized water, dried naturally, and oven dried to constant weight (180 ℃,3 h) for reuse as in example 2, with the results shown in figure 4. It can be seen that the propylene glycol yield can still be maintained above 32% after the propylene glycol is recycled for three times
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and amendments can be made without departing from the principle of the present invention, and these modifications and amendments should also be considered as the protection scope of the present invention.
Claims (10)
1. The method for producing 1, 2-propylene glycol by catalyzing biomass is characterized in that a core-shell structure Beta molecular sieve catalyst is used as a catalyst, biomass is used as a raw material, wherein the core-shell structure Beta molecular sieve catalyst is prepared by dealuminizing a Beta molecular sieve, pt impregnating and Mg (OH) 2 And (3) modification treatment.
2. The method for catalyzing biomass to produce 1, 2-propanediol according to claim 1, wherein the biomass is cellulose, hemicellulose, lignin, corncob, corn stover or sucrose.
3. The method for catalyzing biomass to produce 1, 2-propanediol according to claim 2, wherein the biomass is sucrose.
4. The method for producing 1, 2-propanediol by catalyzing biomass according to any one of claims 1 to 3, wherein the catalyst and the biomass are added into the reactor according to the proportion of the biomass of 100-200 mg, the water of 10-20 mL and the catalyst of 50-300 mg, and the H is introduced 2 Exhaust airThen introducing H with the pressure of 5-6 MPa 2 The hydrogenation catalytic reaction is carried out under the conditions that the reaction temperature is 180-240 ℃ and the reaction time is 30-240 min.
5. The method for catalyzing biomass to produce 1, 2-propanediol according to any one of claims 1 to 4, wherein the preparation method of the core-shell structure Beta molecular sieve catalyst comprises the following steps:
(1) Mixing a Beta molecular sieve with concentrated nitric acid, performing condensation reflux to perform dealumination, washing and drying to obtain a dealuminated and modified Beta molecular sieve deAl-Beta;
(2) Soaking the dealuminized and modified Beta molecular sieve obtained in the step (1) with a chloroplatinic acid solution, standing for aging, drying, roasting at high temperature, mixing the roasted catalyst with water, adding the mixture into a reaction kettle, and carrying out PtO on the catalyst in a high-pressure hydrogen environment 2 Reducing the Pt to obtain a Pt modified catalyst Pt/deAl-Beta;
(3) Mixing the catalyst Pt/deAl-Beta obtained in the step (2), mgO and water, carrying out hydrothermal reaction in a high-pressure hydrogen environment, carrying out solid-liquid separation, drying, grinding into powder, and then carrying out high-temperature roasting to obtain the core-shell structure Beta molecular sieve catalyst Pt/deAl-Beta @ Mg (OH) 2 。
6. The method for catalyzing biomass to produce 1, 2-propanediol according to claim 5, wherein in the step (1), the ratio of the Beta molecular sieve to the concentrated nitric acid is 1g:20mL, and carrying out dealumination for 10-20h by condensation and reflux.
7. The method for producing 1, 2-propanediol by catalyzing biomass according to claim 5, wherein in the step (2), the reduction is a hydrothermal reaction at 200 ℃ and a hydrogen pressure of 5MPa for 4 hn.
8. The method for producing 1, 2-propanediol by catalyzing biomass according to claim 5, wherein in the step (3), mgO is added in an amount of 2.5-12.5 wt% based on the mass of the catalyst Pt/deAl-Beta.
9. The method for producing 1, 2-propanediol by catalyzing biomass according to claim 5, wherein in the step (3), the hydrothermal reaction is carried out for 4h under the conditions of hydrogen pressure of 5MPa, 200 ℃ and 600 r/min.
10. The method for producing 1, 2-propanediol by catalyzing biomass according to claim 5, wherein in the step (3), the high-temperature roasting is carried out at 550 ℃ for 6 hours.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103159587A (en) * | 2011-12-08 | 2013-06-19 | 中国科学院大连化学物理研究所 | Application for catalyst in hydrocracking for biological polyol |
| CN106905109A (en) * | 2017-01-18 | 2017-06-30 | 同济大学 | A kind of method that catalytic hydrogenolysis cellulose produces propane diols |
| CN110483239A (en) * | 2019-08-26 | 2019-11-22 | 同济大学 | A kind of preparation method of propylene glycol |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103159587A (en) * | 2011-12-08 | 2013-06-19 | 中国科学院大连化学物理研究所 | Application for catalyst in hydrocracking for biological polyol |
| CN106905109A (en) * | 2017-01-18 | 2017-06-30 | 同济大学 | A kind of method that catalytic hydrogenolysis cellulose produces propane diols |
| CN110483239A (en) * | 2019-08-26 | 2019-11-22 | 同济大学 | A kind of preparation method of propylene glycol |
Non-Patent Citations (2)
| Title |
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| MINYAN GU等: "Hydrogenolysis of Glucose into Propylene Glycol over Pt/SiO2@Mg(OH)2 Catalyst", CHEMCATCHEM, vol. 12, no. 13, pages 3447 - 3452, XP055786537, DOI: 10.1002/cctc.202000408 * |
| SHIZHUO WANG等: "Glucose Hydrogenolysis into 1, 2-Propanediol Using a Pt/deAl@Mg(OH)2 Catalyst: Expanding the Application of a Core–Shell Structured Catalyst", NANOMATERIALS, vol. 12, pages 1 * |
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