CN109718786B - Catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, and preparation method and application thereof - Google Patents
Catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, a preparation method and application thereof, belonging to the field of acetone condensation catalysts. The catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation comprises the following components in percentage by weight: (1) 2% -25% of copper or its oxide; (2) 8-35% of zinc or its oxide; (3) 2% -40% of cobalt or its oxide; (4) 1-10% of barium or its oxide; (5)30 to 80 percent of alumina; (6) 1% -40% of silicon dioxide; the catalyst of the invention takes copper, zinc, cobalt and the like as load components, properly adjusts the balance of the acidity and alkalinity and the hydrogenation property of the catalyst, prepares a proper catalyst pore channel structure, is used at a lower reaction temperature, has very high conversion rate of acetic ester, less byproducts, high product yield and low energy consumption of subsequent separation. After long-period examination, the catalyst shows ideal stability.
Description
Technical Field
The invention relates to the field of acetone condensation catalysts, and in particular relates to a catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, and a preparation method and application thereof.
Background
Methyl isobutyl ketone (abbreviated as MIBK) is a colorless transparent liquid and has an odor similar to camphor. MIBK is primarily used in medium boiling solvents and organic synthesis feedstocks. In the aspect of solvent use, compared with common solvents (such as acetone, ethyl acetate, cyclohexanone, methyl ethyl ketone and the like), the MIBK has the characteristics of low volatility, good compatibility, no toxicity and the like, and is a high-grade solvent used in the industries of coatings, printing inks, paints, adhesives, epoxy resins and the like. As a paint solvent, the MIBK has excellent performance (good leveling property, hard paint film, moderate volatility, capability of preparing low-viscosity solution and preventing gelation), so that the MIBK has a wide application prospect in high-grade paint. The method has wide application in petroleum dewaxing, metal beneficiation, medicine, atomic absorption spectrum and other aspects. In the aspect of organic synthetic raw materials, the rubber antioxidant 4020 is mainly used for producing synthetic rubber antioxidant 4020, and the antioxidant 4020 is an excellent protective agent for resisting thermal oxidation and fatigue oxidation of rubber, and is developed rapidly in China in recent years. MIBK is also used in small quantities as a specialty surfactant for synthetic inks and agricultural applications.
The existing industrial production method of MIBK mainly comprises an acetone route and an isopropanol route according to raw materials, and in terms of the acetone route, the method also comprises a three-step method and a one-step method, wherein the one-step method has obvious advantages compared with the three-step method. At present, the acetone one-step technique of MIBK abroad is mainly the Taxaco process of Taxaco corporation of germany, the Veba-Chimie process of Veba corporation, the korean DARI corporation technique, the american Eastman technique, the Sasol technique, and the japanese Tokuyama Soda technique, which are relatively mature and have industrial devices built in the united states, western europe, and japan, respectively.
The industrialized one-step method for synthesizing MIBK by acetone generally adopts Pd/resin catalyst, can obtain higher MIBK yield, but has short service life, resin is not high temperature resistant and is difficult to regenerate, the development of the catalyst is not interrupted in the long-term research process of methyl isobutyl ketone, the research aspect of the catalyst in the field of MIBK synthesis is greatly developed, and the future research focuses on further researching and developing high-performance industrial catalyst to further synthesize MIBK with high yield and conversion rate under non-harsh process conditions, thereby shortening the process flow and improving the product yield.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation. In particular to a catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, a preparation method and application thereof. The catalyst is a copper-based catalyst with excellent activity and yield, is low in cost, and can be used for producing MIBK and high value-added diisobutyl ketone (DIBK).
One of the objects of the present invention is to provide a catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, which comprises the following components by weight percent:
(1) 2% -25% of copper or its oxide;
(2) 8-35% of zinc or its oxide;
(3) 2% -40% of cobalt or its oxide;
(4) 1-10% of barium or its oxide;
(5)30 to 80 percent of alumina;
(6)1 to 40 percent of silicon dioxide.
Preferably, the catalyst may comprise the following components in weight percent:
(1) 10% -20% of copper or its oxide;
(2) 10% -25% of zinc or its oxide;
(3) 12% -24% of cobalt or its oxide;
(4) 2-5% of barium or its oxide;
(5)40 to 55 percent of alumina;
(6)5 to 15 percent of silicon dioxide.
In order to obtain more excellent activity and yield, the weight ratio of copper to zinc can be 1 (0.7-2.5), and the weight ratio of cobalt to barium can be 1 (0.1-0.8). The inventors have found that at this ratio the catalyst has the best synergy between the hydrogenation active centre, the acidic site and the basic site.
Another object of the present invention is to provide a method for preparing the catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, which comprises the following steps:
(1) mixing the alumina precursor and sesbania powder in required amount; wherein, the sesbania powder can play a role in lubrication; the dosage of the sesbania powder is 0.5-5% of the mass of the aluminum oxide precursor;
(2) dropwise adding the silicon dioxide precursor and a proper amount of dilute nitric acid in required amount, and uniformly mixing; the carrier can be modified by adding the silicon dioxide precursor, and the dilute nitric acid plays a role in adhesion; wherein, the amount of the silicon dioxide precursor is 3 to 38 percent of the mass of the aluminum oxide precursor, and preferably 3 to 20 percent; the volume concentration of the dilute nitric acid can be 5-30%; the using amount of the dilute nitric acid is 3-15% of the mass of the aluminum oxide precursor;
(3) extruding and drying the solid obtained in the step (2), roasting at 400-950 ℃, and forming to obtain a carrier of the catalyst;
(4) loading the catalyst by an isometric impregnation method; dissolving soluble salts of copper, zinc, cobalt and barium with required dosage in water to form a salt mixed solution; the metal dosage can be calculated according to the content of the final catalyst metal;
(5) pouring the salt mixed solution with the required dosage into a catalyst carrier, quickly shaking, uniformly mixing, standing for 0.5-12 hours, drying, and roasting at 400-950 ℃ to obtain the oxidation state of the catalyst;
(6) reducing the oxidation state catalyst obtained in step (5) to said catalyst. Specifically, the reduction may be carried out using hydrogen or a mixed gas of hydrogen and nitrogen.
The method comprises the steps of loading a catalyst by an isometric impregnation method, knowing the content of each metal element according to the required catalyst composition, calculating the mass of required metal salt according to the content and the mass of a used catalyst carrier, testing the consumption of water required for filling pore channels of the carrier by the isometric impregnation method, dissolving the metal salt in the water with the quantity, and then carrying out impregnation and reduction to obtain the catalyst with the corresponding content.
The carrier used in the invention can use a wide variety of carrier precursors, and the precursor of the alumina can be selected from at least one of pseudo-boehmite and boehmite according to the industrial availability and the expected effect; the precursor of the silica is silica sol.
The soluble salts of copper, zinc, cobalt and barium are copper nitrate, zinc nitrate, cobalt nitrate and barium nitrate.
The invention also aims to provide the specific application of the catalyst for preparing the methyl isobutyl ketone and the diisobutyl ketone by acetone condensation, such as the application in the reaction for preparing the methyl isobutyl ketone and the diisobutyl ketone by acetone condensation.
The catalyst of the invention is applied to the reaction of preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, and the specific hydrogenation process scheme can be as follows: acetone and hydrogen are used as raw materials, the molar ratio of the hydrogen to the acetone is (15-60): 1, the reaction temperature is 170-260 ℃, the reaction pressure is 1.0-4.5 MPa, and the liquid volume space velocity of the acetone is 0.1-1.0 h-1。
The shape of the catalyst can be various, such as spherical, strip, columnar, annular and the like, the size is 0.3-15 mm, more preferably 0.5-3 mm, and the requirement of the size is mainly based on the design of the fixed bed reactor, so that the fixed bed reactor is convenient to install, and the requirement of reducing the pressure of a bed layer is met.
The catalyst of the present invention is reduced before use, the reducing gas may be hydrogen gas, a mixture of hydrogen gas and nitrogen gas, the hydrogen content in the mixture of hydrogen and nitrogen gas may be any content, for example, 2 vol% to 80 vol%, or a higher content gas may be used. From the viewpoint of temperature control of catalyst reduction, a mixed gas having a low hydrogen content is preferred. The larger the space velocity of the gas, the better. The air speed is large, the heat generated by the reaction can be quickly removed in time, the temperature of the catalyst bed is kept stable, and the catalyst is not damaged by temperature runaway. For example, the space velocity of the mixed gas is 300-5000 m3/m3·h-1. The temperature of reduction can be determined according to the composition of the specific catalyst, and for the catalyst provided by the invention, the temperature of a catalyst bed layer can be gradually increased at the speed of 5-20 ℃/h, preferably 5-10 ℃/h, the catalyst bed layer stays at 200 ℃ for 2-8 hours, then the temperature of the catalyst bed layer is gradually increased at the speed of 5-20 ℃/h, preferably 5-10 ℃/h, until the temperature reaches 300-500 ℃, and the catalyst bed layer is kept at the temperature for 2-48 hours. And then slowly cooling to room temperature, for example, the cooling rate is 5-20 ℃/h. Cooling to room temperature, switching to nitrogen, gradually adding hydrogen into nitrogen, and gradually increasing hydrogen consumption to increase the content of hydrogen in the mixed gasHydrogen content. The amount of hydrogen is adjusted at any time according to the change of the temperature of the catalyst, so that the temperature of a catalyst bed is prevented from being too high, for example, not exceeding 50 ℃. If the catalyst is reduced in the reactor, the temperature of the reduced catalyst is reduced to the reaction temperature, and then the catalyst can be fed for use.
Compared with the similar catalysts reported in literatures and used industrially, the catalyst of the invention has higher activity and excellent yield, and the excellent yield is derived from the characteristics of the catalyst; the catalytic properties of the catalyst are derived from the acidic, basic and hydrogenation properties of the catalyst, which are reflected in the differences in the adsorption and desorption capacities for the reactants, reaction transitions and reaction products. The acidity, the alkalinity and the hydrogenation performance of the catalyst can perform better synergistic effect.
The MIBK is synthesized by one-step method of acetone, the reaction process is that two molecules of acetone are condensed under the action of the surface alkaline site of a catalyst to generate one molecule of diacetone alcohol (DAA), and then the diacetone alcohol is catalyzed by an acid site to be dehydrated to generate the Mesityl Oxide (MO). Finally, the isopropylidene acetone reacts with H under the action of the hydrogenation metal active site2Hydrogenation reduction reaction is carried out to generate MIBK; meanwhile, in the reaction process, acetone may be hydrogenated and reduced into Isopropanol (IPA), and the target product MIBK may be further hydrogenated and reduced into methyl isobutyl carbinol (MIBC), or condensed, dehydrated and hydrogenated with acetone again to generate diisobutyl ketone (DIBK).
Therefore, the metal hydrogenation active center on the catalyst, the acid site and the alkaline site are cooperated to complete the reaction process. Copper and cobalt provide hydrogenation active center, zinc and barium provide basic site, alumina is carrier of catalyst and provides acid site, and silica is used to modify alumina carrier. The preparation process and the content of each component of the catalyst influence the interaction of the three active centers, resulting in completely different reaction results. The catalyst preparation process and the content of each component are the results obtained after continuous optimization. The catalyst takes copper, zinc, cobalt and the like as load components, properly adjusts the balance of the acidity and the basicity and the hydrogenation property of the catalyst, prepares a proper catalyst pore channel structure, is used at a lower reaction temperature, has very high conversion rate of acetic ester, few byproducts, high product yield and low energy consumption of subsequent separation. After long-period examination, the catalyst shows ideal stability. And diisobutyl ketone and methyl isobutyl carbinol with higher added values are produced simultaneously when the methyl isobutyl ketone is produced, and the diisobutyl ketone (DIBK for short) can be used as a solvent of industrial coatings due to high boiling point and low evaporation speed, and also can be used as a dispersing agent for manufacturing organic aerosol, a solvent for refining foods and intermediates of certain medicines and pesticides. The product has no production at home, completely depends on import, belongs to a product with high added value, can fill the blank of domestic production by developing and producing DIBK, saves a large amount of foreign exchange, and has good production benefit.
Detailed Description
The present invention will be further described with reference to the following examples. However, the present invention is not limited to these examples.
All the raw materials are commercially available.
Example 1
240g of pseudo-boehmite was poured into a kneader, and 6g of sesbania powder was added thereto, kneaded and mixed. And then adding 60g of silica sol and 10g of dilute nitric acid with the volume fraction of 20%, kneading into blocks, extruding, drying at 120 ℃, roasting at 400 ℃ for 4 hours to obtain a carrier, and crushing to 0.5-3 mm for later use. The silica sol is manufactured by Shandong ocean chemical industry Co., Ltd, and the model is JN-30. Pseudo-boehmite is produced by Jiangsu three-agent industry Co., Ltd, and has a specific surface area of 290m2The pore volume is 0.9 mL/g.
31.5 g of copper nitrate, 25.5 g of cobalt nitrate, 50.5 g of zinc nitrate and 10g of barium nitrate were dissolved in 45 g of water in a beaker to form a salt mixed solution. The mixed solution was poured into a beaker containing 60g of the catalyst support, shaken and left to stand for 3 hours, followed by drying at 120 ℃ and calcination at 450 ℃ for 3 hours to obtain the oxidation state of the catalyst. Before use, reducing the catalyst by using a mixed gas of 5 vol% of hydrogen and 95 vol% of nitrogen according to a temperature programming mode, wherein the maximum temperature of reduction is 450 ℃, and obtaining a catalyst mark MSG-1 after temperature reduction.
Example 2
Pseudo-thin at 270gThe diaspore is poured into a kneader, then 6g of sesbania powder is added, and the mixture is kneaded and mixed evenly. And then adding 30g of silica sol and 10g of dilute nitric acid with the volume fraction of 20%, kneading into blocks, extruding, drying at 120 ℃, roasting at 450 ℃ for 4 hours to obtain a carrier, and crushing to 0.5-3 mm for later use. The silica sol is manufactured by Shandong ocean chemical industry Co., Ltd, and the model is JN-30. Pseudo-boehmite is produced by Jiangsu three-agent industry Co., Ltd, and has a specific surface area of 290m2The pore volume is 0.9 mL/g.
In a beaker 25.5 grams of copper nitrate, 28.5 grams of cobalt nitrate, 40.0 grams of zinc nitrate and 8 grams of barium nitrate were dissolved in 40 grams of water to form a salt mixed solution. The mixed solution was poured into a beaker containing 60g of the catalyst support, shaken and allowed to stand for 2 hours, followed by drying at 120 ℃ and calcination at 450 ℃ for 3 hours to obtain the oxidation state of the catalyst. Before use, reducing the catalyst by using a mixed gas of 5 vol% of hydrogen and 95 vol% of nitrogen according to a temperature programming mode, wherein the maximum temperature of reduction is 450 ℃, and obtaining a catalyst mark MSG-2 after temperature reduction.
Example 3
290g of pseudo-boehmite was poured into a kneader, and 6g of sesbania powder was added thereto, kneaded and mixed. And then adding 10g of silica sol and 10g of dilute nitric acid with the volume fraction of 20%, kneading into blocks, extruding, drying at 120 ℃, roasting at 450 ℃ for 4 hours to obtain a carrier, and crushing to 0.5-3 mm for later use. The silica sol is manufactured by Shandong ocean chemical industry Co., Ltd, and the model is JN-30. Pseudo-boehmite is produced by Jiangsu three-agent industry Co., Ltd, and has a specific surface area of 290m2The pore volume is 0.9 mL/g.
In a beaker, 20.5 g of copper nitrate, 40.5 g of cobalt nitrate, 25.5 g of zinc nitrate and 3 g of barium nitrate were dissolved in 45 g of water to form a salt mixed solution. The mixed solution was poured into a beaker containing 60g of the catalyst support, shaken and left to stand for 3 hours, then dried at 120 ℃ and calcined at 500 ℃ for 3 hours to obtain the oxidation state of the catalyst. Before use, reducing the catalyst by using a mixed gas of 5 vol% of hydrogen and 95 vol% of nitrogen according to a temperature programming mode, wherein the maximum temperature of reduction is 350 ℃, and obtaining a catalyst mark MSG-3 after temperature reduction.
Example 4
220g of pseudo-boehmite was poured into a kneaderThen, 6g of sesbania powder was added, kneaded and mixed. And then adding 80g of silica sol and 10g of dilute nitric acid with the volume fraction of 20%, kneading into blocks, extruding, drying at 120 ℃, roasting at 460 ℃ for 3 hours to obtain a carrier, and crushing to 0.5-3 mm for later use. The silica sol is manufactured by Shandong ocean chemical industry Co., Ltd, and the model is JN-30. Pseudo-boehmite is produced by Jiangsu three-agent industry Co., Ltd, and has a specific surface area of 290m2The pore volume is 0.9 mL/g.
In a beaker, 28.5 g of copper nitrate, 45.5 g of cobalt nitrate, 28.5 g of zinc nitrate and 4 g of barium nitrate were dissolved in 50 g of water to form a salt mixed solution. The mixed solution was poured into a beaker containing 60g of the catalyst support, shaken and left to stand for 4 hours, then dried at 120 ℃ and calcined at 450 ℃ for 2 hours to obtain the oxidation state of the catalyst. Before use, reducing the catalyst by using a mixed gas of 5 vol% of hydrogen and 95 vol% of nitrogen according to a temperature programming mode, wherein the maximum temperature of reduction is 450 ℃, and obtaining a catalyst mark MSG-4 after temperature reduction.
Example 5
This example is an example of catalyst evaluation.
The catalyst is filled in an oil bath controlled isothermal fixed bed reactor, acetone is metered by a metering pump and mixed with hydrogen metered by a gas mass flow meter, the mixture enters the reactor, flows through a catalyst bed layer and reacts under the catalytic action of the catalyst, and the reaction conditions are as follows: the reaction temperature is 180 ℃, the reaction pressure is 1.0MPa, and the space velocity is 0.5h-1The mass ratio of hydrogen to acetone was 30: 1.
The test results are shown in table 1 below.
TABLE 1 test results
As can be seen from the results in Table 1, the catalyst of the present invention has high conversion rate, and simultaneously produces diisobutyl ketone and methyl isobutyl carbinol with higher added value while producing methyl isobutyl ketone. The catalyst MSG-1 is subjected to a stability assessment test for 1000 hours, and shows ideal stability. The characterization analysis shows that the catalyst after the evaluation test has no obvious change in the crystal grain and texture parameters, only stores a small amount of low molecular organic matter, and has no graphitized carbon deposit.
Claims (10)
1. A catalyst for preparing methyl isobutyl ketone and diisobutyl ketone by acetone condensation, which is characterized by comprising the following components in percentage by weight:
(1) 2% -25% of copper or its oxide;
(2) 8-35% of zinc or its oxide;
(3) 2% -40% of cobalt or its oxide;
(4) 1-10% of barium or its oxide;
(5)30 to 80 percent of alumina;
(6) 1% -40% of silicon dioxide;
the catalyst is prepared by an isometric impregnation method.
2. The catalyst for the condensation of acetone to prepare methyl isobutyl ketone and diisobutyl ketone according to claim 1, wherein the catalyst comprises the following components in weight percent:
(1) 10% -20% of copper or its oxide;
(2) 10% -25% of zinc or its oxide;
(3) 12% -24% of cobalt or its oxide;
(4) 2-5% of barium or its oxide;
(5)40 to 55 percent of alumina;
(6)5 to 15 percent of silicon dioxide.
3. The catalyst for the preparation of methyl isobutyl ketone and diisobutyl ketone by acetone condensation according to claim 1 or 2, wherein the weight ratio of copper to zinc is 1: 0.7-2.5, and the weight ratio of cobalt to barium is 1: 0.1-0.8.
4. A process for preparing a catalyst for the condensation of acetone to methyl isobutyl ketone and diisobutyl ketone according to any one of claims 1 to 3, comprising the steps of:
(1) mixing the alumina precursor and sesbania powder in required amount;
(2) dropwise adding the silicon dioxide precursor and the dilute nitric acid with required dosage, and uniformly mixing;
(3) extruding and drying the solid obtained in the step (2), and then roasting and forming to obtain the carrier of the catalyst;
(4) loading the catalyst by an isometric impregnation method; dissolving soluble salts of copper, zinc, cobalt and barium with required dosage in water to form a salt mixed solution;
(5) pouring the mixed solution into a catalyst carrier, quickly shaking, uniformly mixing, standing, drying and roasting to obtain the oxidation state of the catalyst;
(6) reducing the oxidation state catalyst obtained in step (5) to said catalyst.
5. The method of claim 4, wherein the catalyst is prepared by condensing acetone to obtain methylisobutylketone and diisobutyl ketone, and the method comprises the following steps:
in the step (1), the dosage of the sesbania powder is 0.5-5% of the mass of the alumina precursor.
6. The method of claim 4, wherein the catalyst is prepared by condensing acetone to obtain methylisobutylketone and diisobutyl ketone, and the method comprises the following steps:
in the step (2), the amount of the silicon dioxide precursor is 3-38% of the mass of the aluminum oxide precursor; the volume concentration of the dilute nitric acid is 5-30%; the dosage of the dilute nitric acid is 3-15% of the mass of the alumina precursor.
7. The method of claim 4, wherein the catalyst is prepared by condensing acetone to obtain methylisobutylketone and diisobutyl ketone, and the method comprises the following steps:
the alumina precursor is selected from at least one of pseudo-boehmite and boehmite.
8. The method of claim 4, wherein the catalyst is prepared by condensing acetone to obtain methylisobutylketone and diisobutyl ketone, and the method comprises the following steps:
the silicon dioxide precursor is silica sol, and the soluble salts of copper, zinc, cobalt and barium are copper nitrate, zinc nitrate, cobalt nitrate and barium nitrate.
9. The method of claim 4, wherein the catalyst is prepared by condensing acetone to obtain methylisobutylketone and diisobutyl ketone, and the method comprises the following steps:
in the step (3) and the step (5), the roasting temperature is 400-950 ℃.
10. The use of the catalyst for the preparation of methylisobutylketone and diisobutyl ketone by acetone condensation according to any one of claims 1 to 3 or the catalyst prepared by the preparation method according to any one of claims 4 to 9 in the reaction of methylisobutylketone and diisobutyl ketone by acetone condensation, comprising:
acetone and hydrogen are used as raw materials, the molar ratio of the hydrogen to the acetone is (15-60): 1, the reaction temperature is 170-260 ℃, the reaction pressure is 1.0-4.5 MPa, and the liquid volume space velocity of the acetone is 0.1-1.0 h-1。
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