CN108435241B - H beta zeolite catalyst and preparation method thereof, and method and equipment for preparing o-nitroacetophenone from o-nitroethylbenzene - Google Patents
H beta zeolite catalyst and preparation method thereof, and method and equipment for preparing o-nitroacetophenone from o-nitroethylbenzene Download PDFInfo
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- CN108435241B CN108435241B CN201810247124.8A CN201810247124A CN108435241B CN 108435241 B CN108435241 B CN 108435241B CN 201810247124 A CN201810247124 A CN 201810247124A CN 108435241 B CN108435241 B CN 108435241B
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- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
- B01J29/76—Iron group metals or copper
- B01J29/7615—Zeolite Beta
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- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- B01J37/10—Heat treatment in the presence of water, e.g. steam
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- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
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- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
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Abstract
The invention relates to an H beta zeolite catalyst, a preparation method thereof, a method for preparing o-nitroacetophenone from o-nitroethylbenzene and equipment, and relates to the field of chemistry. The H beta zeolite catalyst is used for preparing o-nitroacetophenone by carrying out ozone-induced catalytic oxidation on o-nitroethylbenzene, and comprises a carrier, a first metal and a second metal, wherein the first metal and the second metal are loaded on the carrier, the carrier is H beta zeolite, tetraethylammonium bromide, water, aluminum hydroxide and sodium hydroxide are mixed, silica sol is added into a mixed solution for mixing, crystallization is carried out for 24-27H under the hydrothermal condition of 100-140 ℃, crystallization is carried out for 24-27H under the hydrothermal condition of 150-180 ℃, and then cooling, suction filtration, washing and drying are carried out on obtained filter residue.
Description
Technical Field
The invention relates to the field of chemistry, and in particular relates to an H beta zeolite catalyst and a preparation method thereof, and a method and equipment for preparing o-nitroacetophenone from o-nitroethylbenzene.
Background
O-nitroacetophenone (ONAP) is an important organic synthesis intermediate, and is widely used for synthesizing medicines, pesticides, photosensitive materials and chiral intermediates. The method for obtaining ketone group by controlling the direct oxidation depth of o-nitroethylbenzene side chain alpha-C is the most common production method for preparing o-nitroacetophenone. Early selection of some very oxidizing chemical oxidants, such as: KMnO4, H2O2 and the like, and the chemical oxidation method has the more prominent defects of high reagent consumption, large waste liquid treatment capacity and high production cost. At present, metalloporphyrin and transition metal salt biomimetic catalysts are used in industrial production, and high-pressure air is used as an oxygen source, so that the defects of high equipment investment, long oxidation time and tail gas emission cause the loss of nitroethylbenzene raw materials and environmental pollution are overcome. In the research and development process of green oxidation, research on the adoption of an oxidant which does not produce pollution, an effective reaction path and selection of a proper catalyst are important research subjects for realizing the green oxidation.
Disclosure of Invention
The invention aims to provide an H beta zeolite catalyst, which is low in cost and can effectively improve the conversion rate of ozone-induced o-nitroethylbenzene and the selectivity of o-nitroacetophenone.
The invention also aims to provide a preparation method of the H beta zeolite catalyst, which is simple and controllable in operation and can be used for large-scale production.
The invention also aims to provide a method for preparing o-nitroacetophenone from o-nitroethylbenzene, which is characterized in that the o-nitroacetophenone is prepared by catalytically oxidizing o-nitroethylbenzene by using the H beta zeolite catalyst induced by ozone, the conversion rate is high, the yield is good, and the preparation efficiency is effectively improved.
The invention also aims to provide the equipment for preparing the o-nitroacetophenone according to the method, which has the advantages of simple structure, controllable operation, high conversion rate and good yield, and effectively improves the preparation efficiency.
The technical problem to be solved by the invention is realized by adopting the following technical scheme.
The invention provides an H beta zeolite catalyst which is used for preparing o-nitroacetophenone by carrying out ozone-induced catalytic oxidation on o-nitroethylbenzene.
The invention provides a preparation method of the H beta zeolite catalyst, which comprises the following steps:
tetraethyl ammonium bromide, water, aluminum hydroxide and sodium hydroxide are mixed, added with silica sol and mixed, crystallized for 24-27h under the hydrothermal condition of 140 ℃ at 100-.
The invention provides a method for preparing o-nitroacetophenone from o-nitroethylbenzene, which comprises the following steps:
in oxygen and ozone atmosphere, mixing o-nitroethylbenzene, water and the H beta zeolite catalyst, heating to initiate the reaction of o-nitroethylbenzene, cooling to 118-122 ℃ for continuous reaction, freezing, centrifugally filtering the reacted mixture, and recrystallizing with ethanol.
The invention provides equipment for preparing o-nitroacetophenone according to the method, which comprises an oxygen generating device, an ozone generating device, a reaction device, a heating device, a collecting device and an ice bath device, wherein the oxygen generating device is communicated with an air inlet of the reaction device through a first pipeline, the ozone generating device is communicated with the air inlet of the reaction device through a second pipeline, the first pipeline and the second pipeline are respectively provided with a flowmeter, a mixture liquid of o-nitroethylbenzene, water and an H beta zeolite catalyst is arranged in the reaction device, the first pipeline and the second pipeline are inserted below the liquid level of the mixture liquid, the heating device heats the reaction device, an outlet of the reaction device is communicated with the collecting device, the collecting device is provided with an air outlet pipe, the ice bath device is used for freezing the collecting device, substances in the collecting device are used for centrifugal filtration, and ethanol is.
The H beta zeolite catalyst and the preparation method thereof, and the method and the equipment for preparing the o-nitroacetophenone from the o-nitroethylbenzene have the beneficial effects that:
tetraethyl ammonium bromide is used as a template agent, aluminum hydroxide is used as an aluminum source, sodium hydroxide is used for regulation, silica sol is used as a silicon source, and a surface wetting method is adopted to synthesize beta zeolite under a hydrothermal condition. The beta zeolite is used for loading the first metal and the second metal, so that the activity of the catalyst is effectively improved, the operation is simple and controllable, the cost of the catalyst is low, the conversion rate of o-nitroethylbenzene induced by ozone is improved, and the average selectivity of o-nitroacetophenone is more than 87%.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1 shows the apparatus for preparing o-nitroacetophenone provided by the present invention.
A device for preparing o-nitroacetophenone from 10-o-nitroethylbenzene; 1-an oxygen generating device; 2-an ozone generating device; 3-a reaction device; 4-a stirring device; 5-a thermometer; 6-a collecting device; 7-an air outlet pipe; 8-ice bath device; 9-a flow meter; 11-a first conduit; 12-second conduit.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The H beta zeolite catalyst and the preparation method thereof, and the method and the equipment for preparing o-nitroacetophenone from o-nitroethylbenzene according to the embodiments of the present invention are specifically described below.
The invention provides an H beta zeolite catalyst which is used for preparing o-nitroacetophenone by ozone-induced catalytic oxidation of o-nitroethylbenzene. The H beta zeolite catalyst comprises a carrier, a first metal and a second metal, wherein the first metal and the second metal are loaded on the carrier, the carrier is H beta zeolite, the first metal is Cu, Co, Ni, Fe, Zn or Mn, for example, the first metal is Cu, Co or Mn, and the like, the second metal is Co, Ni, Fe, Zn, Mn or Cu, for example, the second metal is Co, Zn or Mn, and the like.
The first metal is supported in an amount of 0.9 to 1.1%, preferably 1%, by weight of the H beta zeolite catalyst, and the activity is good within the above range.
The second metal is supported at a level of from 0.9 to 1.1%, preferably 1%, by weight of the H beta zeolite catalyst. The activity is excellent within the above range.
More preferably, the loading amount of the first metal is equal to that of the second metal, the catalytic activity is optimal, and the selectivity for o-nitroacetophenone is effectively improved.
In a preferred embodiment of the present invention, the H β zeolite catalyst is prepared by a method comprising:
tetraethyl ammonium bromide, water, aluminum hydroxide and sodium hydroxide are mixed, added with silica sol and mixed, crystallized for 24-27h under the hydrothermal condition of 140 ℃ at 100-. Tetraethyl ammonium bromide is used as a template agent, aluminum hydroxide is used as an aluminum source, sodium hydroxide is used for regulation, silica sol is used as a silicon source, and a surface wetting method is adopted to synthesize beta zeolite under a hydrothermal condition.
In the preferred embodiment of the present invention, the drying is performed at a temperature of 118-.
The invention also provides a method for preparing o-nitroacetophenone from o-nitroethylbenzene, which comprises the following steps:
in oxygen and ozone atmosphere, mixing o-nitroethylbenzene with the H beta zeolite catalyst, heating to initiate the reaction of o-nitroethylbenzene, cooling to 118-122 ℃ for continuous reaction, freezing and centrifugally filtering the reacted mixture, and recrystallizing with ethanol. The method mainly uses ozone as an initiator and oxygen as an oxidant, effectively improves the reaction efficiency of the o-nitroethylbenzene by regulating and controlling the proportion and the flow rate of the two, and simultaneously adopts a pure oxygen reaction environment.
In the preferred embodiment of the present invention, the o-nitroethylbenzene reaction is initiated by heating to 150 ℃ and 170 ℃.
In the preferred embodiment of the present invention, the temperature is preferably decreased to 118-122 ℃ to continue the reaction for 12-17 h.
In the preferred embodiment of the present invention, the catalyst is preferably used in an amount of 10 to 15ppm, which is effective for catalyzing o-nitroethylbenzene.
In order to ensure that the reaction effect is good, the invention also provides equipment for preparing o-nitroacetophenone from o-nitroethylbenzene. It includes oxygen generating device, ozone generating device, reaction unit, heating device, collection device and ice bath device, oxygen generating device communicates through first pipeline and reaction unit's air inlet, ozone generating device and reaction unit's air inlet intercommunication, first pipeline is equipped with the flowmeter respectively with the second pipeline, be equipped with adjacent nitroethylbenzene in the reaction unit, the mixture liquid of water and H beta zeolite catalyst, first pipeline inserts below the liquid level of mixture liquid with the second pipeline, heating device heating reaction unit, reaction unit's export and collection device intercommunication, collection device has the outlet duct, ice bath device is used for freezing collection device, the material is used for centrifugal filtration in the collection device, ethanol recrystallization again.
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1
Referring to fig. 1, this embodiment provides an apparatus 10 for preparing o-nitroacetophenone from o-nitroethylbenzene. It comprises an oxygen generator 1, an ozone generator 2, a reactor 3, a heater (not shown), a collector 6 and an ice bath device 8.
Wherein, oxygen generating device 1 communicates through the air inlet of first pipeline 11 with reaction unit 3, ozone generating device 2 communicates through the air inlet of second pipeline 12 with reaction unit 3, first pipeline 11 and second pipeline 12 are equipped with flowmeter 9 respectively, be equipped with the mixture liquid of adjacent nitroethylbenzene, water and H beta zeolite catalyst in the reaction unit 3, first pipeline 11 inserts below the liquid level of mixture liquid with second pipeline 12, heating device heats reaction unit 3, reaction unit 3's export and collection device intercommunication, collection device has outlet duct 7, ice bath device 8 is used for freezing collection device, the material is used for centrifugal filtration in the collection device, ethanol recrystallization again.
Wherein, the oxygen cylinder, the ozone bottle is through parallelly connected intercommunication, saves space, and first pipeline 11 and second pipeline 12 are equipped with flowmeter 9 respectively for observe the flow of oxygen and ozone.
Optionally, the stirring device 4 is arranged in the reaction device 3, so that the reaction is more sufficient, the contact area of the catalyst and the o-nitroethylbenzene is effectively increased, the reaction efficiency is improved, and meanwhile, the mixing is more uniform.
Optionally, a thermometer 5 is arranged inside the reaction device 3, preferably, the thermometer 5 is arranged at the outlet of the reaction device 3, so that the temperature of the reaction is more convenient to control.
In the preferred embodiment of the present invention, the oxygen generator 1 and the ozone generator 2 are an oxygen cylinder and an ozone cylinder, respectively, and the reaction device 3 is a three-neck flask.
Example 2
An H beta zeolite catalyst is used for preparing o-nitroacetophenone by ozone-induced catalytic oxidation of o-nitroethylbenzene, and is prepared by the following method:
the preparation method of the catalyst comprises the following steps:
a. adding a proper amount of tetraethyl ammonium bromide into a small beaker, adding a proper amount of deionized water, adding sodium hydroxide, stirring to completely dissolve the tetraethyl ammonium bromide, adding a proper amount of aluminum hydroxide, and uniformly stirring. A certain amount of silica sol was added to the above mixed solution. Finally, the mixture is transferred into a 100mL stainless steel reaction kettle with a polytetrafluoroethylene lining, is put into an oven at 120 ℃ for crystallization for 24 hours, and is then supplied to a box at 160 ℃ for crystallization for 24 hours. And after crystallization is finished, cooling the stainless steel reaction kettle to room temperature, carrying out suction filtration on the mixture in the stainless steel reaction kettle, washing with deionized water, and drying at 120 ℃ to obtain the H beta zeolite.
b. Soaking a certain amount of zeolite in a solution containing several metal ions, drying after soaking, and roasting for 2h to obtain the supported beta zeolite (1% M1-1% M2-beta), wherein M1 is Cu, M2 is Co, M1 is a first metal, and M2 is a second metal.
Example 3
A method for preparing o-nitroacetophenone from o-nitroethylbenzene comprises the following steps:
the reaction was carried out in the apparatus provided in example 1 with the H beta zeolite catalyst provided in example 2 as a seat catalyst.
Specifically, oxygen is introduced into the first pipeline, ozone is introduced into the second pipeline, in the oxygen and ozone atmosphere, o-nitroethylbenzene, water and an H beta zeolite catalyst are mixed in a reaction device, the mixture is stirred by a stirring device, and after the mixture is uniformly mixed, the temperature is measured by a thermometer, when the mixture is heated to 150 ℃ by a heating device to initiate the o-nitroethylbenzene to react, the temperature is reduced to 120 ℃, and the reaction is continued for 15 hours.
And collecting the reacted mixture through a collecting device, freezing the mixture through an ice bath device, centrifugally filtering the mixture, and recrystallizing the mixture with ethanol to obtain the compound.
In this example, it is calculated that the conversion rate of o-nitroethylbenzene is 72.3%, the selectivity of o-nitroacetophenone is 87.1%, and the loss rate of o-nitroethylbenzene is 3.2%.
Example 5
An H beta zeolite catalyst, the only difference between this example and example 2, is that M1 is Co and M2 is Mn.
Example 6
An H beta zeolite catalyst, the only difference between this example and example 2, is that a fixed amount of silica sol was added to the above mixture. Finally, the mixture is transferred into a 100mL stainless steel reaction kettle with a polytetrafluoroethylene lining, is put into an oven at 110 ℃ for crystallization for 24 hours, and is then supplied to a box at 155 ℃ for crystallization for 24 hours.
Example 7
The only difference between the method for preparing o-nitroacetophenone from o-nitroethylbenzene and the method in example 3 is that the H beta zeolite catalyst provided in example 5 is used, and in this example, the conversion rate of o-nitroethylbenzene is calculated to be 71.8%, the selectivity of o-nitroacetophenone is 86.9%, and the loss rate of o-nitroethylbenzene is 3.5%.
Example 8
The only difference between the method for preparing o-nitroacetophenone from o-nitroethylbenzene and the method in example 3 is that the H beta zeolite catalyst provided in example 6 is used, and in this example, the conversion rate of o-nitroethylbenzene is calculated to be 72.1%, the selectivity of o-nitroacetophenone is 87%, and the loss rate of o-nitroethylbenzene is 3.6%.
In conclusion, the H beta zeolite catalyst provided by the embodiment of the invention can effectively perform ozone-induced catalytic oxidation on o-nitroethylbenzene to prepare o-nitroacetophenone, has low cost, and can effectively improve the conversion rate of the ozone-induced o-nitroethylbenzene and the selectivity of the o-nitroacetophenone. The preparation method of the H beta zeolite catalyst is simple and controllable, can be used for large-scale production, adopts the ozone to induce the H beta zeolite catalyst to catalyze and oxidize the o-nitroethylbenzene to prepare the o-nitroacetophenone, has high conversion rate and good yield, and effectively improves the preparation efficiency. The device for preparing the o-nitroacetophenone by utilizing the principle has the advantages of simple structure, controllable operation, high conversion rate and good yield, and effectively improves the preparation efficiency.
The embodiments described above are some, but not all embodiments of the invention. The detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Claims (9)
1. A method for preparing o-nitroacetophenone from o-nitroethylbenzene is characterized by comprising the following steps:
in oxygen and ozone atmosphere, mixing o-nitroethylbenzene, water and an H beta zeolite catalyst, heating, after the reaction of the o-nitroethylbenzene is initiated, cooling to 118-122 ℃ for continuous reaction, freezing, centrifugally filtering and recrystallizing by ethanol;
the H beta zeolite catalyst comprises a carrier, a first metal and a second metal, wherein the first metal and the second metal are loaded on the carrier, the carrier is H beta zeolite, the first metal is Cu or Co, and when the first metal is Cu, the second metal is Co; when the first metal is Co, the second metal is Mn;
the loading amount of the first metal is 0.9-1.1% of the weight of the H beta zeolite catalyst, and the loading amount of the second metal is 0.9-1.1% of the weight of the H beta zeolite catalyst.
2. The method as claimed in claim 1, wherein the o-nitroethylbenzene reaction is initiated by heating to 150 ℃ and 170 ℃.
3. The method as claimed in claim 1, wherein the reaction is continued for 12-17h by reducing the temperature to 118-122 ℃.
4. The process of claim 1 wherein the first metal is present at a loading of 1% by weight of the H β zeolite catalyst.
5. The process of claim 1 wherein the second metal is present at a loading of 1% by weight of the H β zeolite catalyst.
6. The method of claim 1, wherein the loading of the first metal is equal to the loading of the second metal.
7. The method of any one of claims 1-6, wherein the H β zeolite is prepared by the following method of preparation: tetraethyl ammonium bromide, water, aluminum hydroxide and sodium hydroxide are mixed, added with silica sol and mixed, firstly crystallized for 24-27h under the hydrothermal condition of 140 ℃ and 100 ℃, and then crystallized for 24-27h under the hydrothermal condition of 180 ℃ and 150 ℃, cooled, filtered, and the obtained filter residue is washed and dried.
8. The method as claimed in claim 7, wherein the drying is carried out at 125 ℃ 118-.
9. The method of claim 7, wherein the drying is performed at 120 ℃.
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