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CN113713829A - Preparation method of sec-butyl acetate hydrogenation catalyst - Google Patents

Preparation method of sec-butyl acetate hydrogenation catalyst Download PDF

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Publication number
CN113713829A
CN113713829A CN202111176849.0A CN202111176849A CN113713829A CN 113713829 A CN113713829 A CN 113713829A CN 202111176849 A CN202111176849 A CN 202111176849A CN 113713829 A CN113713829 A CN 113713829A
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butyl acetate
hydrogenation catalyst
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毛进池
葛立军
王磐
郭为磊
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Kairui Environmental Protection Technology Co ltd
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/889—Manganese, technetium or rhenium
    • B01J23/8892—Manganese
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/03—Precipitation; Co-precipitation
    • B01J37/031—Precipitation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment
    • B01J37/082—Decomposition and pyrolysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2523/00—Constitutive chemical elements of heterogeneous catalysts

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Abstract

The invention relates to the technical field of catalyst preparation, and provides a preparation method of a sec-butyl acetate hydrogenation catalyst, which comprises the following steps: s1, preparing a solution A: adding water into the aluminum hydroxide dry glue to prepare an aluminum hydroxide suspension, and heating and stirring to uniformly disperse the aluminum hydroxide suspension; s2, adding a nitrate solution and a sodium hydroxide solution into the solution A, and carrying out a precipitation reaction; s3, after the precipitation reaction is finished, preserving heat and stirring for aging reaction to obtain a precipitate; s4, filtering, washing and drying the precipitate obtained in the step S3, roasting the precipitate into oxide, and crushing the oxide into powder; and S5, tabletting the powder and then roasting for the second time to obtain the catalyst. Through above-mentioned technical scheme, solved prior art catalyst catalysis effect not good, the trouble problem of waste liquid treatment.

Description

Preparation method of sec-butyl acetate hydrogenation catalyst
Technical Field
The invention relates to the technical field of catalyst preparation, in particular to a preparation method of a sec-butyl acetate hydrogenation catalyst.
Background
Sec-butanol, also known as 2-butanol, of formula C4H10O, a colorless transparent liquid, with a wine-like odor. The product can be used as an intermediate for producing methyl ethyl ketone, for preparing butyl acetate and sec-butyl ester, can be used as a plasticizer, a mineral dressing agent, a herbicide, a solvent and the like, and can also be used for preparing a flotation agent, a spice and a wetting agent, so that sec-butyl alcohol has higher application value in industrial production.
The traditional production method of sec-butyl alcohol is a hydration method, and the sec-butyl alcohol is obtained by carrying out hydration refining on raw material n-butene by sulfuric acid after pretreatment. The other is ion exchange resin hydration method, which takes n-butene as raw material and acid cation exchange resin as catalyst to carry out liquid phase esterification with organic acid, then carries out hydrolysis and rectification to obtain the product, and has low conversion rate and high energy consumption. With the continuous improvement of the preparation process, the preparation of sec-butyl alcohol and the co-production of ethanol by sec-butyl acetate hydrogenation catalysis is more and more concerned by researchers and chemical enterprises, but the problems that the catalytic activity of the catalyst for hydrogenation reaction is low, the product quality is not easy to control, and the post-treatment of waste liquid is complex are gradually exposed.
The invention discloses a catalyst for sec-butyl acetate hydrogenation reaction, a preparation method and application thereof (application number is 201911316655.9). The hydrogenation reaction catalyst has low catalytic activity, and after the sec-butyl acetate hydrogenation reaction is catalyzed, the post-treatment of the generated waste liquid is troublesome, so that the catalyst is not beneficial to industrial production.
Disclosure of Invention
The invention provides a preparation method of a sec-butyl acetate hydrogenation catalyst, which solves the problems of poor catalytic effect and troublesome waste liquid treatment of the catalyst in the related technology.
The technical scheme of the invention is as follows:
a preparation method of a sec-butyl acetate hydrogenation catalyst comprises the following steps:
s1, preparing a solution A: adding water into the aluminum hydroxide dry glue to prepare an aluminum hydroxide suspension, and heating and stirring to uniformly disperse the aluminum hydroxide suspension;
s2, adding a nitrate solution and a sodium hydroxide solution into the solution A, and carrying out a precipitation reaction;
s3, after the precipitation reaction is finished, preserving heat and stirring for aging reaction to obtain a precipitate;
s4, filtering, washing and drying the precipitate obtained in the step S3, roasting the precipitate into oxide, and crushing the oxide into powder;
and S5, tabletting the powder and then roasting for the second time to obtain the catalyst.
As a further technical scheme, the mass ratio of the aluminum hydroxide dry glue to the water is 1 (9-12).
As a further technical scheme, in the step S1, the temperature is raised to 60-70 ℃.
As a further technical scheme, in the step S2, the nitrate solution comprises a mixture of copper nitrate, zinc nitrate, manganese nitrate and water in a mass ratio of (1.5-2): 1.1-1.2): 1- (16-18).
As a further technical scheme, in the step S2, the mass concentration of the sodium hydroxide solution is 20% to 30%.
As a further technical scheme, in the step S2, the precipitation reaction time is controlled to be 4 h.
As a further technical scheme, in the precipitation reaction process, the materials are added for 8 times, and the nitrate solution and the aluminum hydroxide solution are added firstly each time.
As a further technical scheme, in the step S2, the temperature of the precipitation reaction is 70-80 ℃.
As a further technical scheme, in the step S3, the ageing reaction temperature is 80-85 ℃, and the stirring is carried out for 5-6 h.
As a further technical scheme, in the step S4, the roasting temperature is 500-600 ℃, and the roasting time is 3-4 h.
As a further technical scheme, the drying temperature is 100-105 ℃, and the drying time is 8-10 h.
As a further technical scheme, the secondary roasting temperature is 500-600 ℃, and the roasting time is 1-2 h.
The invention has the beneficial effects that:
1. the catalyst prepared by the coprecipitation method has the CuO content of about 40 percent,the specific surface area is large and can reach 170-176m2The catalytic activity is high, under the experimental conditions of the invention, the conversion rate of sec-butyl acetate is about 94-96%, the selectivity of sec-butyl alcohol is 99.5-99.8%, and the amount of waste liquid after the reaction is finished is small and easy to treat.
2. In the synthesis process of the catalyst, the manganese oxide is added, and experiments show that a proper amount of manganese oxide can replace copper oxide to achieve a good catalytic effect. According to experimental researches, the invention discovers that the catalyst obtained by one-time feeding has small specific surface area and low catalytic activity, but the catalytic activity is not changed but reduced by more times of feeding. In addition, the invention carries out secondary roasting after tabletting, thus improving the specific surface area and the reaction activity of the catalyst.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any inventive step, are intended to be within the scope of the present invention.
Example 1
Preparation of a sec-butyl acetate hydrogenation catalyst:
s1, preparing a solution A: adding 50g of water into 4.6g of aluminum hydroxide dry glue to prepare an aluminum hydroxide suspension, and heating to 70 ℃ and stirring to uniformly disperse the aluminum hydroxide suspension;
s2, weighing 23.6g of copper nitrate, 17.8g of zinc nitrate and 15.6g of manganese nitrate solution, mixing with 250g of water and uniformly stirring to obtain a nitrate solution, weighing 16.8g of sodium hydroxide, mixing with 50g of water and uniformly stirring to obtain a sodium hydroxide solution, adding a nitrate solution and a sodium hydroxide solution into the solution A for precipitation reaction, controlling the precipitation reaction temperature to be 75 ℃, adding the sodium hydroxide solution and the nitrate solution into the solution A for eight times, adding 38g of the nitrate solution for the first seven times and 8g of the sodium hydroxide solution for the last time, and adding the rest of the nitrate solution and the rest of the sodium hydroxide solution for the last time respectively;
s3, after the precipitation reaction is finished, keeping the temperature at 80 ℃ and stirring for 5 hours for aging reaction to obtain a precipitate;
s4, filtering and washing the precipitate obtained in the step S3, drying the precipitate at 100 ℃ for 10 hours, roasting the dried precipitate at 500 ℃ in a muffle furnace for 4 hours to form an oxide, and crushing the oxide into powder;
and S5, tabletting the powder, and roasting the powder at 500 ℃ for 2h to obtain the catalyst.
Example 2
Preparation of a sec-butyl acetate hydrogenation catalyst:
s1, preparing a solution A: adding 50g of water into 5g of aluminum hydroxide dry glue to prepare an aluminum hydroxide suspension, and heating to 60 ℃ and stirring to uniformly disperse the aluminum hydroxide suspension;
s2, weighing 22.5g of copper nitrate, 18g of zinc nitrate and 15g of manganese nitrate solution, mixing with 240g of water and uniformly stirring to obtain a nitrate solution, weighing 12.5g of sodium hydroxide, mixing with 50g of water and uniformly stirring to obtain a sodium hydroxide solution, adding a nitrate solution and a sodium hydroxide solution into the solution A, carrying out precipitation reaction, controlling the precipitation reaction temperature to be 70 ℃, adding the sodium hydroxide solution and the nitrate solution into the solution A eight times, adding 37g of the nitrate solution into the solution A every half hour, adding 7.8g of the sodium hydroxide solution into the solution A for the first seven times, and adding the rest of the nitrate solution and the rest of the sodium hydroxide solution into the solution A for the last time;
s3, after the precipitation reaction is finished, keeping the temperature at 85 ℃ and stirring for 5 hours to carry out aging reaction to obtain a precipitate;
s4, filtering and washing the precipitate obtained in the S3, drying the precipitate at 105 ℃ for 8 hours, roasting the dried precipitate at 600 ℃ in a muffle furnace for 3.5 hours to form an oxide, and crushing the oxide into powder;
and S5, tabletting the powder, and roasting for the second time in a muffle furnace at 600 ℃ for 1h to obtain the catalyst.
Example 3
Preparation of a sec-butyl acetate hydrogenation catalyst:
s1, preparing a solution A: adding 60g of water into 5g of aluminum hydroxide dry glue to prepare an aluminum hydroxide suspension, and heating to 65 ℃ and stirring to uniformly disperse the aluminum hydroxide suspension;
s2, weighing 30g of copper nitrate, 16.5g of zinc nitrate and 15g of manganese nitrate solution, mixing the copper nitrate solution with 270g of water and uniformly stirring to obtain a nitrate solution, weighing 25g of sodium hydroxide, mixing the sodium hydroxide solution with 50g of water and uniformly stirring to obtain a sodium hydroxide solution, simultaneously adding a nitrate solution and a sodium hydroxide solution into the solution A, carrying out precipitation reaction, controlling the precipitation reaction temperature to be 65 ℃, adding the sodium hydroxide solution and the nitrate solution into the solution A eight times, adding 41.4g of the nitrate solution into the solution A every half hour, adding 9.4g of the sodium hydroxide solution into the solution A for the first seven times, and adding the rest of the nitrate solution and the rest of the sodium hydroxide solution into the solution A for the last time respectively;
s3, after the precipitation reaction is finished, keeping the temperature at 83 ℃ and stirring for 6 hours to carry out aging reaction to obtain a precipitate;
s4, filtering and washing the precipitate obtained in the S3, drying the precipitate at 105 ℃ for 9 hours, roasting the dried precipitate at 550 ℃ in a muffle furnace for 3.5 hours to form an oxide, and crushing the oxide into powder;
and S5, tabletting the powder, and roasting at 550 ℃ for a second time in a muffle furnace for 1h to obtain the catalyst.
Example 4
Preparation of a sec-butyl acetate hydrogenation catalyst:
s1, preparing a solution A: adding 50g of water into 5.2g of aluminum hydroxide dry glue to prepare an aluminum hydroxide suspension, and heating to 70 ℃ and stirring to uniformly disperse the aluminum hydroxide suspension;
s2, weighing 24.1g of copper nitrate, 17.9g of zinc nitrate and 15.5g of manganese nitrate solution, mixing the copper nitrate solution with 263g of water and uniformly stirring to obtain a nitrate solution, weighing 15g of sodium hydroxide, mixing the sodium hydroxide solution with 50g of water and uniformly stirring to obtain a sodium hydroxide solution, adding a nitrate solution and a sodium hydroxide solution into the solution A for precipitation reaction, controlling the precipitation reaction temperature to be 75 ℃, adding the sodium hydroxide solution and the nitrate solution into the solution A for eight times, adding 40g of the nitrate solution into the solution A every half hour, adding 8.1g of the sodium hydroxide solution into the solution A for the first seven times, and adding the rest of the nitrate solution and the rest of the sodium hydroxide solution into the solution A for the last time;
s3, after the precipitation reaction is finished, preserving heat at 82 ℃ and stirring for 5.5 hours for aging reaction to obtain a precipitate;
s4, filtering and washing the precipitate obtained in the step S3, drying the precipitate at 103 ℃ for 10 hours, roasting the dried precipitate at 500 ℃ in a muffle furnace for 4 hours to form an oxide, and crushing the oxide into powder;
and S5, tabletting the powder, and roasting the powder at 500 ℃ for 2h to obtain the catalyst.
Comparative example 1
S1, dissolving: weighing 36.8gMn (NO)3)2、25.4gCu(NO3)2·3H2O and 4.6g of pseudo-boehmite are mixed, stirred and dissolved to prepare a saturated solution;
s2, precipitation: preparing 16.8g of NaOH into a 40% NaOH solution, adding the NaOH solution into the solution obtained in S1, stirring for 1 hour, and precipitating;
s3, pouring the precipitate into a filter funnel, and vacuumizing for 2 hours to obtain a mud-like substance;
s4, extruding the mud into strips;
s5, drying the strips in an oven at 120 ℃ for 1 h;
and S6, baking and burning the dried strip-shaped object in a muffle furnace at 400 ℃ for 4h, and cooling to obtain the catalyst.
Comparative example 2
The same procedure as in example 1 was repeated except that manganese nitrate was replaced with copper nitrate in an equal amount to that in example 1.
Comparative example 3
The same procedure as in example 1 was repeated except that sodium hydroxide was replaced with an equal amount of sodium carbonate as compared with example 1.
Comparative example 4
In comparison with example 1, the nitrate solution and the sodium hydroxide solution were added to solution a at a time during the precipitation reaction, and the rest was the same as example 1.
Comparative example 5
Compared with the example 1, the nitrate solution and the sodium hydroxide solution are added into the solution A by 16 times in the precipitation reaction, the addition amount of each time is half of that of the example 1, the precipitation reaction is still controlled to be completed within 4 hours, and the rest is the same as that of the example 1.
Comparative example 6
The same procedure as in example 1 was repeated except that the second baking was not performed after the tabletting, as in example 1.
The activity of the catalysts prepared in the examples and the comparative examples is evaluated, and the hydrogenation reaction conditions of sec-butyl acetate are as follows: 10g of catalyst filling, 5MPa of pressure, 5g/h of sec-butyl acetate, 39L/h of hydrogen flow and 40 of hydrogen/ester.
TABLE 1 catalyst activity of examples and comparative examples
Figure BDA0003295937060000051
The catalyst prepared by the invention has large specific surface area which can reach 170-176m2The catalytic activity is high, under the experimental conditions of the invention, the conversion rate of sec-butyl acetate is about 94-96%, the selectivity of sec-butyl alcohol is 99.5-99.8%, and the amount of waste liquid after the reaction is finished is small and easy to treat. The catalyst prepared according to the conventional experimental method in comparative example 1 has a small surface area and poor catalytic performance. In comparative example 2, the manganese nitrate is replaced by the same amount of copper nitrate, the specific surface area of the prepared catalyst is not changed greatly, but the catalytic activity is reduced, and since the copper oxide plays a key role in catalytically synthesizing sec-butyl alcohol, the invention discovers that the proper amount of manganese oxide can promote the reaction better through comparative example 2. In comparative example 3, the catalyst prepared by replacing sodium hydroxide with sodium carbonate had a large specific surface area, but the catalytic activity was rather decreased. In comparative example 4, the one-time addition reaction not only lowered the specific surface area of the catalyst but also deteriorated the catalytic activity. In comparative example 5, although the number of times of addition was increased, no better effect was produced on the catalytic activity, but the preparation process was complicated.
The present invention is not limited to the above preferred embodiments, and any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. The preparation method of the sec-butyl acetate hydrogenation catalyst is characterized by comprising the following steps:
s1, preparing a solution A: adding water into the aluminum hydroxide dry glue to prepare an aluminum hydroxide suspension, and heating and stirring to uniformly disperse the aluminum hydroxide suspension;
s2, adding a nitrate solution and a sodium hydroxide solution into the solution A, and carrying out a precipitation reaction;
s3, after the precipitation reaction is finished, preserving heat and stirring for aging reaction to obtain a precipitate;
s4, filtering, washing and drying the precipitate obtained in the step S3, roasting the precipitate into oxide, and crushing the oxide into powder;
and S5, tabletting the powder and then roasting for the second time to obtain the catalyst.
2. The preparation method of the sec-butyl acetate hydrogenation catalyst according to claim 1, wherein the mass ratio of the aluminum hydroxide dry glue to the water is 1 (9-12).
3. The preparation method of the sec-butyl acetate hydrogenation catalyst according to claim 1, wherein the temperature in the step S1 is raised to 60-70 ℃.
4. The preparation method of sec-butyl acetate hydrogenation catalyst as claimed in claim 1, wherein in the step S2, the nitrate solution comprises a mixture of copper nitrate, zinc nitrate, manganese nitrate and water in a mass ratio of (1.5-2): 1.1-1.2):1 (16-18).
5. The preparation method of the sec-butyl acetate hydrogenation catalyst according to claim 1, wherein in the step S2, the mass concentration of the sodium hydroxide solution is 20% -30%.
6. The preparation method of the sec-butyl acetate hydrogenation catalyst as claimed in claim 1, wherein in the step S2, the precipitation reaction time is controlled to be 4 h.
7. The preparation method of the sec-butyl acetate hydrogenation catalyst as claimed in claim 6, wherein in the precipitation reaction process, the added materials are added in 8 times, and the nitrate solution and the aluminum hydroxide solution are added in each time.
8. The preparation method of the sec-butyl acetate hydrogenation catalyst as claimed in claim 1, wherein the temperature of the precipitation reaction in the step S2 is 70-80 ℃.
9. The preparation method of the sec-butyl acetate hydrogenation catalyst as claimed in claim 1, wherein in the step S3, the aging reaction temperature is 80-85 ℃, and the stirring is carried out for 5-6 h.
10. The preparation method of sec-butyl acetate hydrogenation catalyst as claimed in claim 1, wherein in the step S4, the calcination temperature is 500-600 ℃ and the calcination time is 3-4 h.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115228456A (en) * 2021-12-17 2022-10-25 中国石油天然气股份有限公司 High-efficiency catalyst for catalytic decomposition of nitrous oxide
CN115228456B (en) * 2021-12-17 2023-07-28 中国石油天然气股份有限公司 High-efficiency catalyst for catalytic decomposition of nitrous oxide

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