CN107899575B - Nano-gold catalyst for generating ester by one-step oxidation esterification of aldehyde and alcohol and preparation method and application thereof - Google Patents
Nano-gold catalyst for generating ester by one-step oxidation esterification of aldehyde and alcohol and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of chemical catalysis, in particular to a nanogold catalyst for generating ester by one-step oxidation and esterification of aldehyde and alcohol and a preparation method and application thereof. The nano gold catalyst takes Au as an active component and takes a cerium-based composite solid solution as a carrier, and the loading amount of the Au accounts for 0.1-2 wt% of the total mass of the Au and the carrier; the cerium-based composite solid solution is a Ce-Zr solid solution, a Ce-Co solid solution, a Ce-Fe solid solution, a Ce-Mn solid solution, a Ce-Ni solid solution or a Ce-Fe-Cu solid solution. The invention has the advantages of 98.3-99.8 percent of aldehyde conversion rate and 97.6-99.7 percent of ester selectivity, simple operation, higher conversion rate and better product selectivity, and the catalyst is easy and convenient to recover, thereby greatly improving the stability of the reaction and the process economy.
Description
Technical Field
The invention relates to the technical field of chemical catalysis, in particular to a nanogold catalyst for generating ester by one-step oxidation and esterification of aldehyde and alcohol and a preparation method and application thereof.
Background
Ester compounds are important chemical and organic synthesis intermediates, and the traditional synthesis method is to prepare acid or acid derivatives by oxidizing aldehyde or alcohol and then esterify the acid or acid derivatives, but the preparation process is complex and many toxic byproducts are generated in the process.
Since 1970, there have been patents relating to catalysts for the one-step oxidative esterification of aldehydes to esters, such as gold-based catalysts described in JP20000154164, JP2003192632, JP 2003361086; ｃA palladium-based catalyst as described in JP-B-4-72578, JP-A-61-243044, US 4638085. Japanese patent JP2005008557 mentions that the conversion rate of the reaction for synthesizing ester by one-step oxidative esterification of methacrolein is only 32.8% by using Au catalyst, and the conversion rate is low, so that the industrial production cannot be realized.
The catalyst in the above patent generates a large amount of by-products in the reaction process, and has the disadvantages of easy inactivation, complex recovery operation, slow reaction speed, low conversion rate and the like.
Chinese patent CN101618328A discloses a supported nano-gold catalyst and a preparation method thereof. The supported nano-gold catalyst consists of active components of nano-gold, an auxiliary agent and gamma-Al2O3And (3) a carrier. The preparation method comprises the steps of gamma-Al2O3Carrier modification, nano-gold active component impregnation, reduction, washing and drying. The patent uses gamma-Al2O3Carriers for conversion of trace amounts of carbon monoxide, albeit containing Fe2O3、MnO2、CuO、Co2O3、CeO2Or an auxiliary agent such as NiO, but the component of the carrier is Fe2O3、MnO2、CuO、Co2O3、CeO2The function and content of NiO are different from the invention.
Chinese patent CN103801326A discloses a supported nano-gold catalyst and a preparation method thereof. The preparation method of the supported nano gold catalyst comprises the steps of contacting a carrier with a tetrachloroauric acid aqueous solution in a rotary evaporator under the condition of deposition and precipitation to obtain a mixed solution containing solid precipitates, then evaporating to remove water, and sequentially drying and calcining to obtain a solid. The carrier of the supported nano gold catalyst is hydroxyl ferric oxide, cerium oxide and sodium niobate. In the patent, iron oxyhydroxide, ferric oxide and cerium oxide are used as carriers, the carrier is weak in alkalinity, and the number of supplied active oxygen is small, so that the reaction is not facilitated.
Disclosure of Invention
The invention aims to provide a nanogold catalyst for generating ester by one-step oxidation esterification of aldehyde and alcohol, which has the characteristics of high reaction speed, high conversion rate, good selectivity and long service life.
The nano gold catalyst for generating ester by one-step oxidation esterification of aldehyde and alcohol takes Au as an active component and a cerium-based composite solid solution as a carrier, and the loading amount of the Au accounts for 0.1-2 wt% of the total mass of the Au and the carrier; the cerium-based composite solid solution is a Ce-Zr solid solution, a Ce-Co solid solution, a Ce-Fe solid solution, a Ce-Mn solid solution, a Ce-Ni solid solution or a Ce-Fe-Cu solid solution.
The preparation method of the nanogold catalyst for generating ester by one-step oxidation esterification of aldehyde and alcohol comprises the following steps:
(1) preparation of the support
Dissolving soluble salt of metal in an ionic liquid solution, adding a sodium hydroxide solution, carrying out hydrothermal reaction, centrifuging to obtain a solid, drying, and calcining to obtain a carrier;
(2) preparation of nano gold catalyst
In HAuCl4And (2) sequentially adding a protective agent and a reducing agent into the aqueous solution, then adding the carrier obtained in the step (1), adjusting the pH value by using an HCl solution, stirring at room temperature, filtering, washing, drying and roasting to obtain the nano-gold catalyst.
Wherein:
in the step (1), the ratio of the sum of the metal mole number to the mole number of the ionic liquid to the mole number of the sodium hydroxide is 1:1-3: 5-10.
In the step (1), the soluble salt is nitrate, hydrochloride or sulfate.
In the step (1), the ionic liquid consists of anions and cations, wherein the anions are Cl-、Br-、BF4 -、PF6 -、TfO-(CF3SO3 -)、NfO-(C4F9SO3 -)、SbF6 -、AsF6 -、CH3COO-、NO3 -Or SO4 -The cation is [ NR ]4]+、[bmim]+、[emim]+、[Rpy]+、[C8mim]+、[C10mim]+、[C12mim]+Or [ C14mim]+。
In the step (1), the hydrothermal reaction temperature is 100-200 ℃, and the hydrothermal reaction time is 20-28 h; the drying temperature is 40-100 ℃, and the drying time is 10-14 h; the calcination temperature is 350-450 ℃, and the calcination time is 2-6 h.
In the step (2), the protective agent is PVA, and the reducing agent is NaBH4(ii) a The mass ratio of PVA to Au is 1:2, NaBH4The molar ratio to Au was 5: 1.
In the step (2), HCl solution is adopted to adjust the pH value to 4-6.
In the step (2), stirring at room temperature for 0.5-4h, drying at 40-100 ℃ for 10-14 h; the roasting temperature is 250-300 ℃, and the roasting time is 2-6 h.
The invention discloses an application of a nanogold catalyst for generating ester by one-step oxidation esterification of aldehyde and alcohol, which comprises the following steps: adding the nano gold catalyst into aldehyde and alcohol solutions in the presence of 0.1-0.5MPa of oxygen, and heating and refluxing.
The aldehydes and alcohols can be any saturated aldehydes and alcohols.
The invention has the following beneficial effects:
(1) the invention takes the ionic liquid as a template agent and an ion enhancer when preparing the carrier, and has the function of structure guidance. Soluble salt of metal is dissolved in the ionic liquid solution, so that the dosage of alkali is reduced, the prepared carrier has a micro-pore structure, the specific surface area of the carrier is increased, and the loading capacity of the carrier is enhanced; and the nano gold particles are loaded in the micro-pore structure of the carrier, so that the increase of the nano gold particles is effectively prevented. In addition, the ionic liquid can enhance the interaction between the carrier and the nano-gold particles, so that the nano-gold particles are more stable, the service life of the catalyst is longer, and the catalytic activity is better.
The invention dissolves the metal soluble salt in the ionic liquid large environment, but does not add the ionic liquid solution into the metal soluble salt solution, thereby not only reducing the dosage of alkali, but also leading the metal soluble salt to be completely acted by the ionic liquid solution in the process of forming the carrier.
(2) The pore size of the carrier is controlled by adjusting the hydrothermal reaction temperature, the type and the dosage of the ionic liquid, and the specific surface area of the carrier is increased;
(3) according to the invention, Zr, Co, Fe and other metal doped cerium-based composite solid solution is used as a carrier, and metal atoms of Zr, Co, Fe and the like enter a cerium oxide crystal lattice, so that the surface of the carrier has more oxygen cavities, the quantity of active oxygen is increased, the loading capacity of the catalyst carrier is enhanced, the reaction performance of the catalyst is improved, the catalytic activity of the catalyst is improved, and the recovery mode of the catalyst is improved.
(4) The invention has the advantages of 98.3-99.8 percent of aldehyde conversion rate and 97.6-99.7 percent of ester selectivity, simple operation, higher conversion rate and better product selectivity, and greatly improves the stability of reaction and process economy.
Drawings
Fig. 1 is a transmission electron microscope image of the magnetic nanogold catalyst in example 1.
Detailed Description
The present invention is further described below with reference to examples.
Example 1
The preparation method of the nanogold catalyst for generating the ester by one-step oxidation esterification of the aldehyde and the alcohol comprises the following steps:
(1) preparation of the support
1.8g of [ C10mim]Dissolving Cl ionic liquid in 10ml deionized water, dissolving 0.87g of cerium nitrate and 0.46g of zirconyl nitrate in the ionic liquid, adding a sodium hydroxide solution prepared from 0.6g of sodium hydroxide and 70g of water, putting the mixed solution into a 100ml polytetrafluoroethylene-lined hydrothermal kettle, carrying out hydrothermal reaction for 24h at 100 ℃, centrifuging and washing, drying the obtained solid for 12h at 80 ℃, and calcining for 4h at 400 ℃ to obtain the rod-shaped cerium-zirconium solid solution carrier with the pore structure.
(2) Preparation of nano gold catalyst
Is prepared by a sol precipitation method, takes PVA as a protective agent and NaBH4Is a reducing agent. Stirring to 1X 10- 4mol/LHAuCl4Adding 1 wt.% PVA aqueous solution into the aqueous solution to make PVA/Au (wt/wt) ═ 0.5:1, stirring for 5 minutes, and then adding 0.1mol/L NaBH4The aqueous solution becomes wine red liquid, wherein NaBH4Au (mol/mol) ═ 5: 1. And (3) stirring for half an hour, and adding the cerium-zirconium solid solution carrier obtained in the step (1). The solution was adjusted to pH 5 with 0.1mol/L HCl, stirred at room temperature for 1h, then filtered by washing with deionized water until no residual Cl remained in the solution-Drying the obtained solid in a drying oven at 80 ℃ for 12h, and finally roasting at 300 ℃ for 4h to obtain the nano-gold catalyst, wherein the loading amount of Au is 1 wt.%. The transmission electron micrograph of the obtained nanogold catalyst is shown in fig. 1.
The application of the nanogold catalyst for generating the ester by one-step oxidative esterification of aldehyde and alcohol comprises the following steps:
the reaction is carried out in a 50ml stainless steel jacketed pressure-isolated batch reactor according to the conventional process. The catalyst, isobutyraldehyde and MeOH were added. The mass flow meter controls the stable oxygen flow rate to be 10mol/min, and a good gas distribution state is kept by using the distributor. The magnetic stirrer heats and stirs to keep good contact of gas phase, liquid phase and solid phase, tail gas at a reaction outlet is cooled and reflows by a condenser pipe to prevent volatilization of raw materials and reaction products, and a pressure stabilizing valve is connected behind the condenser pipe to control the pressure in the reactor. After the reaction device is sealed, firstly introducing oxygen to 0.3MPa, then starting circulating water bath heating, starting stirring, and starting reaction. After reacting for 2h, stopping gas intake and stirring, closing heating, introducing circulating cold water, cooling, exhausting gas, and taking out a sample for gas chromatography analysis. The test data are shown in Table 1.
Example 2
The procedure of example 1 was otherwise repeated except that zirconyl nitrate in example 1 was changed to ferric nitrate to prepare a cerium-iron solid solution carrier.
Example 3
The zirconyl nitrate in example 1 was changed to ferric nitrate, [ C ]10mim]The amount of Cl was changed to 3.6g, and a cerium-iron solid solution carrier was prepared, and the rest of the procedure was the same as in example 1.
Example 4
The zirconyl nitrate in example 1 was changed to ferric nitrate and the ionic liquid was changed to [ C ]14mim]Cl, in an amount of 2.2g, a cerium-iron solid solution support was prepared, and the remaining steps were the same as in example 1.
Example 5
The zirconyl nitrate in example 1 was changed to cobalt nitrate and the ionic liquid was changed to [ C ]10mim]BF4The amount of the cerium-cobalt solid solution carrier was changed to 2.2g, and the remaining steps were the same as in example 1.
Example 6
The zirconyl nitrate in example 1 was changed to cobalt nitrate and the ionic liquid was changed to [ C ]10mim]BF4The amount of the cerium-cobalt solid solution carrier was changed to 4.4g, and the remaining steps were the same as in example 1.
Example 7
The zirconyl nitrate in example 1 was changed to cobalt nitrate and the ionic liquid was changed to [ emim]SbF6The dosage is changed to 2.6g to prepare cerium cobalt solidThe carrier was dissolved and the procedure was as in example 1.
Example 8
The zirconyl nitrate in example 1 was changed to manganese nitrate and the ionic liquid was changed to [ C ]8mim]PF6The amount of the cerium-manganese solid solution carrier was changed to 2.4g, and the remaining steps were the same as in example 1.
Example 9
The zirconyl nitrate in example 1 was changed to manganese nitrate and the ionic liquid was changed to [ C ]8mim]SbF6The amount of the cerium-manganese solid solution carrier was changed to 3.0g, and the remaining steps were the same as in example 1.
Example 10
The zirconyl nitrate in example 1 was changed to nickel nitrate and the ionic liquid was changed to [ C ]14mim]SbF6The amount of cerium-nickel solid solution carrier was changed to 3.6g, and the remaining steps were the same as in example 1.
Example 11
The zirconyl nitrate in example 1 was changed to nickel nitrate and the ionic liquid was changed to [ Rpy]NO3The amount of the cerium-nickel solid solution carrier was changed to 1.6g, and the remaining steps were the same as in example 1.
Example 12
The ionic liquid of example 1 was mixed with a mixture of 1.8g of [ C ]10mim]Cl was changed to 3.6g of [ C ]12mim]Cl, 0.87g of cerium nitrate and 0.46g of zirconyl nitrate were changed to 1.32g of cerium nitrate, 0.606g of ferric nitrate and 0.935g of copper nitrate, and a hydrothermal reaction was carried out at 140 ℃ to prepare a Ce-Fe-Cu solid solution carrier, and the rest of the procedure was the same as in example 1.
The test data for examples 1-12 are shown in Table 1.
TABLE 1 test data sheet
| Examples | Conversion ratio of aldehyde (%) | Selection of estersProperty (%) |
| 1 | 98.6 | 98.2 |
| 2 | 98.7 | 98.1 |
| 3 | 99.1 | 98.6 |
| 4 | 99.5 | 99.3 |
| 5 | 99.4 | 99.1 |
| 6 | 99.5 | 99.2 |
| 7 | 98.9 | 98.4 |
| 8 | 99.3 | 98.9 |
| 9 | 99.4 | 99.1 |
| 10 | 99.8 | 99.7 |
| 11 | 98.3 | 97.6 |
| 12 | 99.4 | 99.0 |
Wherein:
Claims (8)
1. a preparation method of a nanogold catalyst for generating ester by one-step oxidation esterification of aldehyde and alcohol is characterized by comprising the following steps:
(1) preparation of the support
Dissolving soluble salt of metal in an ionic liquid solution, adding a sodium hydroxide solution, carrying out hydrothermal reaction, centrifuging to obtain a solid, drying, and calcining to obtain a carrier;
(2) preparation of nano gold catalyst
In HAuCl4Sequentially adding a protective agent and a reducing agent into the aqueous solution, then adding the carrier obtained in the step (1), adjusting the pH value, stirring at room temperature, filtering, washing, drying and roasting to obtain a nano gold catalyst;
the nano gold catalyst takes Au as an active component and takes a cerium-based composite solid solution as a carrier, and the loading amount of the Au accounts for 0.1-2 wt% of the total mass of the Au and the carrier; the cerium-based composite solid solution is a Ce-Zr solid solution, a Ce-Co solid solution, a Ce-Fe solid solution, a Ce-Mn solid solution, a Ce-Ni solid solution or a Ce-Fe-Cu solid solution;
step (1)) The ionic liquid consists of anion and cation, and the anion is Cl-、Br-、BF4 -、PF6 -、TfO-(CF3SO3 -)、NfO-(C4F9SO3 -)、SbF6 -、AsF6 -、CH3COO-、NO3 -Or SO4 2-The cation is [ NR ]4]+、[bmim]+、[emim]+、[Rpy]+、[C8mim]+、[C10mim]+、[C12mim]+Or [ C14mim]+。
2. The method for preparing the nanogold catalyst for the one-step oxidative esterification of aldehyde and alcohol to ester according to claim 1, wherein the method comprises the following steps: in the step (1), the mole ratio of the metal, the ionic liquid and the sodium hydroxide is 1:1-3: 5-10.
3. The method for preparing the nanogold catalyst for the one-step oxidative esterification of aldehyde and alcohol to ester according to claim 1, wherein the method comprises the following steps: in the step (1), the soluble salt is nitrate, hydrochloride or sulfate.
4. The method for preparing the nanogold catalyst for the one-step oxidative esterification of aldehyde and alcohol to ester according to claim 1, wherein the method comprises the following steps: in the step (1), the hydrothermal reaction temperature is 100-200 ℃, and the hydrothermal reaction time is 20-28 h; the drying temperature is 40-100 ℃, and the drying time is 10-14 h; the calcination temperature is 350-450 ℃, and the calcination time is 2-6 h.
5. The method for preparing the nanogold catalyst for the one-step oxidative esterification of aldehyde and alcohol to ester according to claim 1, wherein the method comprises the following steps: in the step (2), the protective agent is PVA, and the reducing agent is NaBH4(ii) a The mass ratio of PVA to Au is 1:2, NaBH4The molar ratio to Au was 5: 1.
6. The method for preparing the nanogold catalyst for the one-step oxidative esterification of aldehyde and alcohol to ester according to claim 1, wherein the method comprises the following steps: in the step (2), HCl solution is adopted to adjust the pH value to 4-6.
7. The method for preparing the nanogold catalyst for the one-step oxidative esterification of aldehyde and alcohol to ester according to claim 1, wherein the method comprises the following steps: in the step (2), stirring at room temperature for 0.5-4h, drying at 40-100 ℃ for 10-14 h; the roasting temperature is 250-300 ℃, and the roasting time is 2-6 h.
8. The application of the nanogold catalyst for the one-step oxidative esterification of aldehyde and alcohol to ester by adopting the preparation method of claim 1 is characterized in that: adding the nano gold catalyst into aldehyde and alcohol solutions in the presence of 0.1-0.5MPa of oxygen, and heating and refluxing.
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| CN109772345B (en) * | 2019-01-05 | 2022-03-04 | 山东理工大学 | Preparation of nickel catalyst for synthesizing ester by aldehyde oxidation esterification and application of nickel catalyst and ionic liquid co-catalysis system |
| CN110105207B (en) * | 2019-04-22 | 2022-03-04 | 山东理工大学 | One-step oxidation esterification process and application of p-hydroxybenzaldehyde |
| CN111330574B (en) * | 2020-04-07 | 2023-05-05 | 山东理工大学 | Method for preparing core-shell cerium-gold catalyst by reverse microemulsion method and application of catalyst |
| CN111495390B (en) * | 2020-04-21 | 2023-08-25 | 浙江师范大学 | Supported gold catalyst for synthesizing ester by oxidation and esterification of alcohol/aldehyde compound and preparation and application thereof |
| CN111514930B (en) * | 2020-04-30 | 2023-07-25 | 山东理工大学 | Ionic liquid stable monoatomic catalyst and preparation method and application thereof |
| CN111774069B (en) * | 2020-07-08 | 2023-02-14 | 上海纳米技术及应用国家工程研究中心有限公司 | Manganese-cerium solid solution loaded cobalt catalyst for catalyzing and oxidizing volatile organic compounds by ozone and preparation method and application thereof |
| CN112871167B (en) * | 2021-01-14 | 2022-07-08 | 浙江理工大学 | MOFs (metal-organic frameworks) -packaged ultrafine alloy nanoparticles as well as preparation method and application thereof |
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