CN115106115B - Method for preparing acetone from alkane - Google Patents

Method for preparing acetone from alkane Download PDF

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CN115106115B
CN115106115B CN202110294136.8A CN202110294136A CN115106115B CN 115106115 B CN115106115 B CN 115106115B CN 202110294136 A CN202110294136 A CN 202110294136A CN 115106115 B CN115106115 B CN 115106115B
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catalyst
use according
molecular sieve
isoparaffin
usy
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CN115106115A (en
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李春义
李宁
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China University of Petroleum East China
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China University of Petroleum East China
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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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
    • B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
    • B01J29/0308—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
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    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/041—Mesoporous materials having base exchange properties, e.g. Si/Al-MCM-41
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    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/084—Y-type faujasite
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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
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/085—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing rare earth elements, titanium, zirconium, hafnium, zinc, cadmium, mercury, gallium, indium, thallium, tin or lead
    • B01J29/088—Y-type faujasite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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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
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
    • B01J29/106—Y-type faujasite
    • B—PERFORMING OPERATIONS; TRANSPORTING
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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
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
    • B01J29/14—Iron group metals or copper
    • B01J29/146—Y-type faujasite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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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
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/16—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J29/166—Y-type faujasite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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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
    • B01J29/7007—Zeolite Beta
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/10—After treatment, characterised by the effect to be obtained
    • B01J2229/20—After treatment, characterised by the effect to be obtained to introduce other elements in the catalyst composition comprising the molecular sieve, but not specially in or on the molecular sieve itself
    • 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
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/30—After treatment, characterised by the means used
    • B01J2229/42—Addition of matrix or binder particles
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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Abstract

A method for preparing acetone, comprising: isoparaffin hydrogen peroxide is decomposed under the action of a catalyst to generate acetone and alcohol substances; a catalyst comprising an active component and a carrier, wherein the active component comprises a metal element and/or a zeolite molecular sieve, wherein the metal element comprises Ce, ti, zr, nb, W, V, cr, mo, mn, co, fe, cu, ni, zn and Ag element; the zeolite molecular sieve comprises one or more than two of Y-type molecular sieve, USY-type molecular sieve, ZSM-5 type molecular sieve, beta-type molecular sieve, mordenite and offretite. The isoparaffin hydrogen peroxide can be prepared from isoparaffin through oxidation, and the cost is low.

Description

Method for preparing acetone from alkane
Technical Field
The application relates to a method for preparing acetone, in particular to a method for preparing acetone from alkane hydrogen peroxide, and belongs to the field of chemical industry.
Background
Acetone, also called dimethyl ketone, is the simplest saturated ketone, is also an important organic chemical raw material, is mainly applied to the production of epoxy resin, polycarbonate, organic glass, medicines, pesticides and the like, and can also be directly used as a solvent and produce other solvents.
The production method of acetone mainly comprises fermentation method, organic matter hydration method, propylene oxidation method, isobutyraldehyde oxidation method, etc.
The earliest production method of acetone is a fermentation method, which takes grains or other saccharides as raw materials, obtains sterile fermentation base solution after high-temperature steaming, boiling, sterilizing and disinfecting, then adds specific strains for fermentation, and the fermented liquid is distilled to obtain the acetone. The fermentation method has the advantages of lag technology, high production cost and low efficiency, and the method is basically eliminated at present.
The propylene oxidation method uses oxygen as an oxidant to oxidize propylene into acetone, and uses a catalyst with copper chloride-palladium chloride as an active component to catalyze the propylene to oxidize the acetone, and the catalyst can be recycled through the following reaction. First, propylene will PdCl 2 Reducing to Pd, simultaneously generating acetone and HCl, and re-oxidizing Pd to PdCl by another component CuCl2 on the catalyst 2 While CuCl 2 Is reduced to CuCl, finally the CuCl is treated with HCl and O 2 Under the action of (a) re-oxidation to CuCl2, thereby completing the cycle.
Pd+2CuCl 2 →PdCl 2 +2CuCl
2CuCl+1/2O 2 +2HCl→2CuCl 2 +H 2 O
This method, although having a high acetone yield, is limited by the price of the raw material isobutyraldehyde, and is difficult to be used industrially.
The main process for the current production of acetone is the cumene oxidation process, the main technical authorities of which are KBR, sanjingjingjing and UOP corporation in the united states. The method mainly comprises the production steps of cumene synthesis, cumene peroxidation, cumene peroxide concentration, decomposition, neutralization, product refining and the like. It is reported in literature that cumene peroxide is used as a raw material, the temperature of a reactor is gradually increased along with the flow direction of the raw material, a mixture of the cumene peroxide and the diisopropylbenzene peroxide is generated under the catalysis of concentrated sulfuric acid, the reaction temperature is increased to decompose the diisopropylbenzene peroxide into a mixed solution of acetone and phenol, and products of phenol and acetone are obtained through methods such as rectification. Or, the mixed solution of cumene peroxide and cumene is used as a raw material, the reaction temperature is 40-75 ℃, under the catalysis of organic acid, such as 2-hydroxy-5-methyl-benzenesulfonic acid, 4-hydroxy-benzyl-1, 3-disulfonic acid, 2-hydroxy-5-methoxybenzenesulfonic acid and the like, the mixed solution of dicumyl peroxide and cumene is generated, the reaction temperature is increased to 110-140 ℃, the mixed solution of acetone and phenol is generated, and the acetone product can be obtained after rectification and purification. This method requires a large amount of acid, and the mixed solution after the reaction requires addition of a neutralizing excess of the acid before purification.
Cumene may also be used as a raw material, and a part of cumene is oxidized to cumene peroxide in the presence of oxygen to obtain a mixture of cumene hydroperoxide and cumene. The mixed solution contacts with a non-acidic catalyst, and part of cumene peroxide and unreacted cumene in the mixed solution generate dimethylbenzyl alcohol. The solution containing dimethylbenzyl alcohol is contacted with an acid catalyst to produce alpha-methylstyrene, acetone, and phenol. The method effectively avoids the use of concentrated sulfuric acid and alkaline substances, reduces the corrosion of equipment and reduces the production cost.
The isopropyl benzene method for producing the acetone has the advantages of high product quality, lower raw material and energy consumption and the like, but 2 tons of phenol are required to be co-produced for each 1 ton of acetone production, and the economic benefit of the acetone production method is more easily limited by the supply and demand relation of phenol markets.
Other acetone production methods, such as fermentation, isopropanol dehydrogenation, propylene oxidation, acetylene hydration, acetic acid by-product methods, etc., are difficult to use due to limitations in production efficiency or production cost.
For this purpose, the application is distinguished.
Disclosure of Invention
The application aims to reduce the production cost of acetone and improve the production efficiency.
Another object of the present application is to provide a catalyst for preparing acetone from isoparaffin hydrogen peroxide.
In order to achieve the above purpose, the following technical scheme is adopted:
a method for preparing acetone, comprising: isoparaffin hydrogen peroxide is decomposed under the action of a catalyst to generate acetone and alcohol substances.
The isoparaffin hydrogen peroxide can be prepared by oxidizing isoparaffin as a raw material, the raw material is low in cost, and some byproducts can be used as important components of fuel liquefied gas.
Detailed Description
The method for preparing acetone according to the present application will be described in further detail. And do not limit the scope of the application, which is defined by the claims. Certain disclosed specific details provide a thorough understanding of the various disclosed embodiments. However, one skilled in the relevant art will recognize that embodiments can be practiced without one or more of the specific details, with other materials, etc.
In the description and in the claims, the terms "comprising," including, "and" containing "are to be construed as open-ended, meaning" including, but not limited to, unless the context requires otherwise.
In the present specification, the numerical range indicated by the term "numerical value a to numerical value B" means a range including the end point numerical value A, B.
In the present specification, a numerical range indicated by the use of "above" or "below" means a numerical range including the present number.
Reference in the specification to "an embodiment," "one embodiment/preferred embodiment," "another embodiment/preferred embodiment," or "certain embodiments" or the like means that a particular element described (e.g., a particular feature, structure, or characteristic described in connection with the embodiment) is included in at least one embodiment. Thus, it is not necessary for an "embodiment," "one embodiment," "another embodiment," or "certain embodiments" to refer to the same embodiment. Furthermore, the particular features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. The various features disclosed in the specification may be replaced by alternative features serving the same, equivalent or similar purpose. Thus, unless expressly stated otherwise, the disclosed features are merely general examples of equivalent or similar features.
The experimental procedures, which do not address the specific conditions in the examples below, are generally carried out under conventional conditions or under conditions recommended by the manufacturer. All percentages, ratios, proportions, or parts are by weight unless otherwise indicated.
Definition:
the structural feature of isoparaffins of the present application is that the methyl substituent is in the 2-position, i.e., 2-methylalkane.
The isoparaffin of Cn in the specification means that the total number of carbon atoms of isoparaffin is n. The isomerized alkane having 10 or less refers to an isoparaffin having 10 or less total carbon atoms.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present application. The preferred methods and materials described herein are presented for illustrative purposes only.
On the one handA catalyst for preparing acetone from isoparaffin comprises active component and carrier,
the active component comprises a metal element and/or a zeolite molecular sieve, wherein the metal element comprises Ce, ti, zr, nb, W, V, cr, mo, mn, co, fe, cu, ni, zn and Ag element; the zeolite molecular sieve comprises one or more than two of Y-type molecular sieve, USY-type molecular sieve, ZSM-5 type molecular sieve, beta-type molecular sieve, mordenite and offretite.
The content of the metal element in the catalyst is 0.1 to 40wt%, preferably 0.3 to 20wt%. The weight of the metal element is calculated as the highest valence oxide.
The metal element may be in the form of a metal, or may be a metal oxide, and preferably a metal oxide.
The active component metal element in the catalyst is preferably WO 3 、TiO 2 、MnO x 、MoO x 、CoO x 、FeO x 、CuO x One or more of them.
The zeolite molecular sieve content in the catalyst is 5-80 wt%, preferably 20-50wt%.
In certain embodiments, the zeolite molecular sieve is preferably one of USY, ZSM-5 and beta type molecular sieves, and is present in the catalyst in an amount of from 5% to 80% by weight, preferably from 20% to 50% by weight.
The carrier comprises Al 2 O 3 、SiO 2 Kaolin, diatomaceous earth, mgO, caO and La 2 O 3 One or more of them, preferably Al 2 O 3 、SiO 2 And kaolin, or a mixture of both.
The balance of the catalyst is the weight of the support.
In certain embodiments, in the catalysts for isoparaffin to acetone, the active component is selected from USY molecular sieves or beta-type molecular sieves. The yield of acetone is better.
The catalyst preparation method can adopt the preparation commonly used in the prior art, for example, a method of pulping and then spray granulation can be adopted; or the mixture can be manufactured by a method of extruding strips after kneading; a rolling ball method and the like can also be adopted.
In one embodiment, a method of preparing a catalyst comprises: mixing the substances containing metal elements, molecular sieves and sol containing carrier components, and drying and roasting to obtain the catalyst.
In some embodiments, the preparation method of the catalyst comprises the steps of firstly loading metal elements on a zeolite molecular sieve through an impregnation method, mixing the obtained loaded zeolite molecular sieve with sol containing carrier components, and drying and roasting to obtain the catalyst.
Another partyThe surface of the noodle is provided with a plurality of grooves,a method for preparing acetone, comprising: isoparaffin hydrogen peroxide is decomposed under the action of a catalyst to generate acetone and alcohol substances. The catalyst is used in the reaction process.
In certain embodiments, isoparaffins include C10 or less isoparaffins. Preferably, an isomerized alkane of C7 or less; more preferably isobutane.
In the application, isoparaffin hydrogen peroxide reacts under the action of a catalyst at the reaction temperature controlled within the range of 50-350 ℃ to generate acetone. The preferred reaction temperature is controlled in the range of 90-300 ℃.
In certain embodiments, isoparaffin hydrogen peroxide is reacted under the influence of a catalyst to produce acetone at a reaction temperature controlled in the range of 60-200 ℃.
In certain embodiments, the isoparaffin hydrogen peroxide is contacted with the catalyst for a reaction time of from 0.1s to 2 minutes, preferably from 0.5s to 10s.
The catalytic decomposition reaction of isoparaffin hydrogen peroxide is carried out in a fixed bed, and the average residence time in the catalyst bed obtained by apparent gas velocity calculation is 0.1s-2min, preferably controlled to be 0.5s-10s.
For the reactant which is in liquid state at normal temperature and normal pressure, the reactant enters a fixed bed of the reactor for reaction after being preheated to be in gas state.
In the application, isoparaffin hydrogen peroxide is contacted with the catalyst, and can be converted into acetone and corresponding alcohols in a short time at the temperature of below 200 ℃.
When isoparaffin hydrogen peroxide selects isobutane hydrogen peroxide, the yield of acetone is above 50%. The produced by-product methanol can react with tertiary butanol or isobutene to produce MTBE, and can also be used in MTO and other processes.
In the application, isoparaffin hydrogen peroxide is prepared by oxidizing isoparaffin.
In one embodiment, the isoparaffin is reacted with oxygen at a temperature below 250 ℃. The reaction is preferably carried out at a temperature in the range from 80 to 200 ℃.
In certain embodiments, isoparaffins are reacted with oxygen at a temperature in the range of 80-150 ℃.
The oxidation time of alkane is preferably 10min-10h, more preferably 30min-6h.
Under the above reaction conditions, safety can be ensured, and operation beyond the explosion limit is required. That is, during the isoparaffin peroxidation, the concentration of oxygen is mainly controlled at a low level, so that the reaction mixture is far from the explosion limit range to ensure safety. In the present application, the alkane conversion is controlled to be less than 40%, preferably less than 25%, to ensure that the gas phase oxygen concentration is within a safe range. The reaction pressure is maintained at the saturated vapor pressure of the alkane at the corresponding reaction temperature.
Compared with the prior art for preparing acetone, the acetone preparation method at least comprises the following advantages:
1) The source of the isoparaffin as the raw material of the acetone is wide, and the price is low. The method selects isoparaffin such as isobutane with low price as raw material for preparing the acetone, and has small price fluctuation. As by-product alcohols of the reaction, small molecular alcohols such as methanol, ethanol and the like, or macromolecular alcohols such as propanol, butanol, amyl alcohol and the like have wide application.
2) In the whole preparation process, the temperature is below 350 ℃, the preparation method is mild, the process is simple, the energy consumption is low, and the efficiency is high. The two-step reaction can be completed in two reactors, and the reaction is exothermic, so that not only does not need complex heat supply equipment, but also heat can be taken from the reaction as a heat source in the subsequent separation process, and the fuel consumption is low and the energy consumption is low.
3) Low in the yield of low-value byproducts and good in economic benefit. Taking tert-butane as an example, the target product of the reaction is acetone, and the main byproducts are tert-butanol, methanol and isobutene, which are all raw materials for producing MTBE. CO, CO 2 Few by-products such as methane and water.
The preparation method of acetone and the technical effects obtained according to the present application will be further described below using specific examples.
Example 1
A certain amount of silica Sol (SiO) 2 30% by mass) is placed in a stirring kettle to be stirred, then a certain amount of ZSM molecular sieve is added (the mass fraction of ZSM in the finally obtained catalyst is 30%), stirring is continued for 2 hours, and after the stirring is continued, the catalyst is dried at 120 ℃ and baked at 700 ℃ for 2 hours, and 30% ZSM/SiO can be obtained 2 A catalyst.
Example 2
A certain amount of silica Sol (SiO) 2 30% by mass) is placed in a stirring kettle to be stirred, a certain amount of USY molecular sieve is added (the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), the stirring is continued for 2 hours, and after the stirring is continued for 2 hours, the catalyst is dried at 120 ℃ and baked at 700 ℃ for 2 hours, and 30% USY/SiO can be obtained 2 A catalyst.
Example 3
A certain amount of silica Sol (SiO) 2 30% by mass) of the catalyst is placed in a stirring kettle to be stirred, a certain amount of H beta molecular sieve is added (the mass fraction of the H beta molecular sieve in the finally obtained catalyst is 30%), the catalyst is continuously stirred for 2 hours, and then is dried at 120 ℃ and baked at 700 ℃ for 2 hours, thus obtaining 30% H beta/SiO 2 A catalyst.
Example 4
A certain amount of silica Sol (SiO) 2 30% by mass) is placed in a stirring kettle to be stirred, a certain amount of MCM-41 molecular sieve is added (the mass fraction of the MCM-41 molecular sieve in the finally obtained catalyst is 30%), the stirring is continued for 2 hours, and after the stirring is continued for 2 hours, the catalyst is dried at 120 ℃ and baked at 700 ℃ for 2 hours, and 30% of MCM-41/SiO can be obtained 2 A catalyst.
Example 5
A certain amount of USY molecular sieve catalyst is taken and immersed in a certain amount of ammonium metatungstate solution (so that WO 3 Accounting for 10 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain the WO 3 -USY. A certain amount of silica Sol (SiO) 2 30% by mass) of the mixture is placed in a stirring kettle to be stirred, and a certain amount of WO is added 3 USY (the mass fraction of USY molecular sieve in the finally obtained catalyst is 30%), stirring for 2 hours, drying at 120 ℃ and roasting at 700 ℃ for 2 hours to obtain 10% WO 3 -30％USY/SiO 2 A catalyst.
Example 6
A certain amount of USY molecular sieve catalyst is taken, and a certain amount of ammonium molybdate solution is immersed (so that MoO 3 Accounting for 10 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain MoO 3 -USY. A certain amount of silica Sol (SiO) 2 30% of the mass fraction) is placed in a stirring kettle to be stirred, and a certain amount of MoO is added 3 USY (the mass fraction of USY molecular sieve in the finally obtained catalyst is 30%), stirring for 2 hours, drying at 120 ℃ and roasting at 700 ℃ for 2 hours to obtain 10% MoO 3 -30％USY/SiO 2 A catalyst.
Example 7
And (3) taking a certain amount of USY molecular sieve catalyst, immersing a certain amount of cobalt nitrate solution (CoO accounts for 10% of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain the CoO-USY. A certain amount of silica Sol (SiO) 2 30% by mass) is placed in a stirring kettle to be stirred, a certain amount of CoO-USY (the mass fraction of USY molecular sieve in the finally obtained catalyst is 30%) is added, the mixture is continuously stirred for 2 hours, and then is dried at 120 ℃ and baked at 700 ℃ for 2 hours, thus obtaining 10% CoO-30% USY/SiO 2 A catalyst.
Example 8
And (3) taking a certain amount of USY molecular sieve catalyst, immersing a certain amount of nickel nitrate solution (NiO accounts for 10% of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain NiO-USY. A certain amount of silica Sol (SiO) 2 30% by mass) of the catalyst is placed in a stirring kettle to be stirred, a certain amount of NiO-USY (the mass fraction of USY molecular sieve in the finally obtained catalyst is 30%) is added, the mixture is continuously stirred for 2 hours, and then is dried at 120 ℃ and baked at 700 ℃ for 2 hours, so that 10% of NiO-30% of USY/SiO can be obtained 2 A catalyst.
Example 9
A certain amount of silica Sol (SiO) 2 Adding a certain amount of USY molecular sieve to pulp (accounting for 30% of the total mass of the catalyst), and then adding a certain amount of titanyl sulfate (in the form of TiO) 2 Accounting for 10 percent of the total mass of the catalyst), and spray granulation is carried out after uniform stirring.The solid microspheres are obtained and baked for 2 hours at 700 ℃ to obtain 10 percent TiO 2 -30％USY/SiO 2 A catalyst.
Example 10
Taking a certain amount of USY molecular sieve catalyst, soaking a certain amount of ferric nitrate solution (so that Fe 2 O 3 10% of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain Fe 2 O 3 -USY. A certain amount of silica Sol (SiO) 2 Adding a certain amount of Fe (30% by mass) 2 O 3 Pulping the USY molecular sieve (so that USY accounts for 30% of the total mass of the catalyst), uniformly stirring, and then carrying out spray granulation. The solid microspheres are obtained and baked for 2 hours at 700 ℃ to obtain 10 percent Fe 2 O 3 -30％USY/SiO 2 A catalyst.
Example 11
Taking a certain amount of USY molecular sieve catalyst, impregnating a certain amount of ammonium meta-tungstate and ammonium molybdate solution (so that WO 3 And MoO 3 Each accounting for 5 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain the WO 3 -MoO 3 -USY. A certain amount of silica Sol (SiO) 2 30% by mass) of WO is added 3 -MoO 3 Pulping the USY molecular sieve (so that USY accounts for 30% of the total mass of the catalyst), uniformly stirring, and then carrying out spray granulation. The solid microspheres are obtained and baked for 2 hours at 700 ℃ to obtain 5 percent of WO 3 -5％MoO 3 -30％USY/SiO 2 A catalyst.
Example 12
Taking a certain amount of USY molecular sieve, soaking a certain amount of ammonium metatungstate and ferric nitrate solution (so as to obtain WO 3 And Fe (Fe) 2 O 3 Each accounting for 5 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain the WO 3 -Fe 2 O 3 -USY. A certain amount of silica Sol (SiO) 2 30% by mass) was placed in a beaker and stirred, and a certain amount of WO was added thereto 3 -Fe 2 O 3 USY (the mass fraction of USY molecular sieve in the final catalyst is 30%), stirring for 2h, oven drying at 120deg.C, and calcining at 700deg.C for 2h to obtain5％WO 3 -5％Fe 2 O 3 -30％USY/SiO 2 A catalyst.
Example 13
A certain amount of silica Sol (SiO) 2 Adding a certain amount of USY molecular sieve for pulping (accounting for 30% of the total mass of the catalyst), and adding a certain amount of ammonium molybdate and ferric nitrate solution (so as to enable MoO) 3 And Fe (Fe) 2 O 3 Each accounting for 5 percent of the total mass of the catalyst), and spray granulation is carried out after uniform stirring. The solid microspheres are obtained by roasting at 700 ℃ for 2 hours, drying at 120 ℃ and roasting at 700 ℃ for 2 hours, and 5 percent MoO can be obtained 3 -5％Fe 2 O 3 -30％USY/SiO 2 A catalyst.
Example 14
Placing a certain amount of aluminum sol into a stirring kettle for stirring, adding a certain amount of ZSM molecular sieve (the mass fraction of ZSM in the finally obtained catalyst is 30%), continuously stirring for 2 hours, drying at 120 ℃, and roasting at 700 ℃ for 2 hours to obtain 30% ZSM/Al 2 O 3 A catalyst.
Example 15
Placing a certain amount of aluminum sol into a stirring kettle for stirring, adding a certain amount of H beta molecular sieve (the mass fraction of H beta in the finally obtained catalyst is 30%), continuously stirring for 2 hours, drying at 120 ℃, and roasting at 700 ℃ for 2 hours to obtain 30% H beta/Al 2 O 3 A catalyst.
Example 16
Placing a certain amount of aluminum sol into a stirring kettle, stirring, adding a certain amount of USY molecular sieve (so that the mass fraction of USY in the finally obtained catalyst is 30%), continuously stirring for 2h, drying at 120 ℃, and roasting at 700 ℃ for 2h to obtain 30% USY/Al 2 O 3 A catalyst.
Example 17
A certain amount of USY molecular sieve catalyst is taken and immersed in a certain amount of ammonium metatungstate solution (so that WO 3 Accounting for 10 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain the WO 3 -USY. Taking a certain amount of aluminum sol and a certain amount of WO 3 USY (so that in the final catalystThe USY molecular sieve is 30 percent by mass percent) and is evenly mixed, and is subjected to kneading and strip extrusion. Obtaining a long-strip catalyst, and roasting at 700 ℃ for 2 hours to obtain 10% of WO 3 -30％USY/Al 2 O 3 A catalyst.
Example 18
A certain amount of USY molecular sieve catalyst is taken, and a certain amount of ammonium molybdate solution is immersed (so that MoO 3 Accounting for 10 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain MoO 3 -USY. Taking a certain amount of aluminum sol and a certain amount of MoO 3 And (3) uniformly mixing USY (the mass fraction of USY molecular sieve in the finally obtained catalyst is 30%), and kneading and extruding. Obtaining a long-strip catalyst, and roasting at 700 ℃ for 2 hours to obtain 10% MoO 3 -30％USY/Al 2 O 3 A catalyst.
Example 19
Mixing a certain amount of USY molecular sieve catalyst with a certain amount of aluminum sol (so that the mass fraction of USY molecular sieve in the final catalyst is 30%), adding a certain amount of ferric nitrate (so that Fe 2 O 3 Accounting for 10 percent of the total mass of the catalyst), and after being evenly mixed, the catalyst is kneaded and extruded. Obtaining a long-strip catalyst, and roasting at 700 ℃ for 2 hours to obtain 10% Fe 2 O 3 -30％USY/Al 2 O 3 A catalyst.
Example 20
Taking a certain amount of USY molecular sieve catalyst, impregnating a certain amount of ammonium meta-tungstate and ferric nitrate solution (so that WO 3 And Fe (Fe) 2 O 3 Each accounting for 5 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain the WO 3 -Fe 2 O 3 -USY. Taking a certain amount of pseudo-boehmite and a certain amount of WO 3 -Fe 2 O 3 USY (so that the mass fraction of USY molecular sieve in the final catalyst is 30%) is mixed well and a certain amount of water-rolling balls is added. Obtaining a spherical catalyst, and roasting at 700 ℃ for 2 hours to obtain 5 percent of WO 3 -5％Fe 2 O 3 -30％USY/Al 2 O 3 A catalyst.
Example 21
Mixing a certain amount of USY molecular sieve catalyst with a certain amount of pseudo-boehmite (so that the mass fraction of USY molecular sieve in the final catalyst is 30%) thoroughly, adding a certain amount of ammonium molybdate solution (so that MoO is obtained) 3 5% of the total mass of the catalyst) and a certain amount of ferric nitrate solution (so that Fe is added 2 O 3 Each accounting for 5 percent of the total mass of the catalyst), and the mixture is uniformly mixed and then is rolled. Obtaining a spherical catalyst, and roasting at 700 ℃ for 2 hours to obtain 5% MoO 3 -5％Fe 2 O 3 -30％USY/Al 2 O 3 A catalyst.
Example 22
Preparation of isobutane hydrogen peroxide:
the peroxidation of isobutane takes isobutane and oxygen as raw materials, the oxygen intake is calculated according to the maximum conversion rate of isobutane as 20 percent, the reaction temperature is 120 ℃, the residence time is 2 hours, and the reaction pressure is 2.8Mpa. The results are shown in Table 1.
Example 23
Preparation of isobutane hydrogen peroxide:
the peroxidation of isobutane takes isobutane and oxygen as raw materials, the oxygen intake is calculated according to the maximum conversion rate of isobutane as 20 percent, the reaction temperature is 140 ℃, the residence time is 2 hours, and the reaction pressure is 3.6Mpa. The results are shown in Table 1.
Experimental results for the preparation of isopentyl hydroperoxide by peroxidation of isopentane are shown in examples 3-4.
Example 24
Preparation of isopentane hydrogen peroxide:
the peroxidation of isopentane takes isopentane and oxygen as raw materials, the oxygen inlet amount is calculated according to the maximum conversion rate of isopentane being 20%, the reaction temperature is 120 ℃, the residence time is 2h, and the reaction pressure is 1.02Mpa. The results are shown in Table 2.
Example 25
Preparation of isopentane hydrogen peroxide:
the peroxidation of isopentane takes isopentane and oxygen as raw materials, the oxygen intake is calculated according to the maximum conversion rate of isopentane being 20%, the reaction temperature is 140 ℃, the residence time is 2h, and the reaction pressure is 1.5Mpa. The results are shown in Table 2.
The products obtained in examples 22 to 23 were isolated and purified to give tert-butyl hydroperoxide as shown in Table 1. The products obtained in examples 24 to 25 were isolated and purified to give isopentyl hydroperoxide as shown in Table 2.
TABLE 1
TABLE 2
The isopentyl hydroperoxide or tert-butyl hydroperoxide obtained in examples 22 to 25 was subjected to the following catalytic decomposition reaction. As shown in the data of Table 3, the reaction results of t-butyl hydroperoxide as the reactant, and the catalysts prepared in examples 1-21 were selected during the reaction, respectively, at 140℃for a residence time of 7s. The residence time of the present application is understood to be the contact time of the catalyst with the alkyl hydroperoxide.
The catalysts of examples 1-21 may also be used for the decomposition of the catalyst isopentyl hydroperoxide or tert-butyl hydroperoxide.
Example 26
The isopentyl hydrogen peroxide was used as a starting material, the catalyst of example 19 was used under the same conditions, the reaction temperature was 140℃and the residence time was 7s, and the reaction results were shown in Table 4.
Example 27
The reaction conditions were also the same as in example 26 using isopentyl hydrogen peroxide as a starting material and the reaction results are shown in Table 4.
Example 28
The reaction conditions were also the same as in example 26 using isopentyl hydrogen peroxide as a starting material and the reaction results are shown in Table 4.
Example 29
Preparation of MoO 3 /Al 2 O 3 Catalyst, take a certain amount of Al 2 O 3 After measuring the water absorption, a certain amount of an ammonia heptamolybdate solution is immersed in Al 2 O 3 On a carrier (in MoO) 3 The load is 10wt percent, and after the impregnation is finished, the mixture is dried at 120 ℃ and baked for 2 hours at 700 ℃ to obtain MoO 3 /Al 2 O 3 A catalyst.
In a fixed bed reactor, tert-butyl hydroperoxide is used as raw material, and the MoO prepared by the method is used 3 /Al 2 O 3 As a catalyst, the reaction temperature was 130℃and the residence time was 7s, and the catalyst was stabilized for 1 hour after charging the raw materials and sampled and analyzed.
Examples 30 to 33 all used 10wt% MoO of the catalyst except for this example 3 /Al 2 O 3 。
Example 30
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, moO is used 3 /Al 2 O 3 As a catalyst, the reaction temperature was 140℃and the residence time was 7s, and the catalyst was stabilized for 1 hour after charging the raw materials and sampled and analyzed.
Example 31
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, moO is used 3 /Al 2 O 3 As a catalyst, the reaction temperature was 150℃and the residence time was 7s, and the catalyst was stabilized for 1 hour after charging the raw materials and sampled and analyzed.
Example 32
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, moO is used 3 /Al 2 O 3 As a catalyst, the reaction temperature was 130℃and the residence time was 27s, and the catalyst was stabilized for 1 hour after charging the raw materials and sampled and analyzed.
Example 33
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, moO is used 3 /Al 2 O 3 As a catalyst, the catalyst was subjected to sampling analysis after charging the raw material at a reaction temperature of 130℃and a residence time of 54 s.
Experiments on the reaction conditions are shown in comparative examples 4-5 and examples 29-33, and the results are shown in Table 5.
Comparative example 1
In a fixed bed reactor, tert-butyl hydroperoxide was used as a raw material, quartz sand was charged in the reactor as a catalyst, the reaction temperature was 140 ℃, the residence time of the reaction raw material in the bed was 7s, and the reaction raw material was stabilized for 1 hour after the introduction of the raw material, and sampling analysis was performed, as shown in table 1.
Comparative example 2
In a fixed bed reactor, tert-butyl hydroperoxide is taken as a raw material, and SiO is filled in the reactor 2 As a catalyst, the reaction temperature was 140℃and the residence time of the reaction raw material in the bed was 7s, and the sample was analyzed by stabilization for 1 hour after charging the raw material, as shown in Table 1.
Comparative example 3
In a fixed bed reactor, an aqueous solution of tert-butyl hydroperoxide is used as a raw material, and Al is filled in the reactor 2 O 3 As a catalyst, the reaction temperature was 140℃and the residence time of the reaction raw material in the bed was 7s, and the sample was analyzed by stabilization for 1 hour after charging the raw material, as shown in Table 1.
Comparative example 4
In a fixed penetrating reactor, tert-butyl hydroperoxide is taken as a raw material, moO is taken as a raw material 3 /Al 2 O 3 As a catalyst, the reaction temperature was 40℃and the residence time was 7s, and the catalyst was stabilized for 1 hour after charging the raw materials and sampled and analyzed.
Comparative example 5
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, moO is used 3 /Al 2 O 3 As a catalyst, the reaction temperature was 130℃and the residence time was 0.05s, and the reaction mixture was stabilized for 1 hour after charging the raw materials, and sampling analysis was performed.
TABLE 3 Table 3
TABLE 4 Table 4
TABLE 5

Claims (23)

1. The application of a catalyst in preparing acetone from isoparaffin comprises an active component and a carrier, wherein,
the active component comprises a metal element, or
The active component comprises metal elements and zeolite molecular sieves,
wherein the metal element comprises WO 3 、TiO 2 、MnO x 、MoO x 、CoO x 、FeO x 、CuO x One or more of the following; the zeolite molecular sieve comprises one or more than two of Y-type molecular sieve, USY-type molecular sieve, ZSM-5 type molecular sieve, beta-type molecular sieve, mordenite and offretite.
2. Use according to claim 1, characterized in that the content of metallic elements in the catalyst is 0.1-40wt%, the weight of metallic elements being calculated as the highest oxides.
3. Use according to claim 1, characterized in that the zeolite molecular sieve content of the catalyst is 5-80 wt%.
4. Use according to any one of claims 1 to 3, wherein the zeolite molecular sieve comprises one of USY, ZSM-5 and beta type molecular sieves.
5. Use according to any one of claims 1-3, characterized in that the carrier comprises Al 2 O 3 、SiO 2 Kaolin, diatomaceous earth, mgO, caO and La 2 O 3 One or more of them.
6. Use according to any one of claims 1-3, characterized in that the carrier comprises Al 2 O 3 、SiO 2 And kaolin, or a mixture of both.
7. Use according to claim 1, characterized in that the content of metallic elements in the catalyst is between 0.3 and 20wt%, the weight of metallic elements being calculated as the highest oxides.
8. Use according to claim 1, characterized in that the zeolite molecular sieve content of the catalyst is 20-50wt%.
9. The use according to claim 1, wherein isoparaffinic hydrogen peroxide is decomposed to acetone and alcohols under the action of a catalyst;
isoparaffins include isoparaffins having a C10 or lower.
10. Use according to claim 9, wherein isoparaffinic hydrogen peroxide is reacted under the action of a catalyst to form acetone at a reaction temperature controlled in the range of 50-350 ℃.
11. Use according to claim 9 or 10, characterized in that the contact reaction time of isoparaffinic hydrogen peroxide with the catalyst is between 0.1s and 2min.
12. Use according to claim 9 or 10, characterized in that the catalytic decomposition of isoparaffinic hydrogen peroxide is carried out in a fixed bed, the superficial gas velocity being calculated to give an average residence time in the catalyst bed of 0.1s-2min.
13. The use according to claim 9 or 10, wherein isoparaffinic hydrogen peroxide is prepared by oxidation of isoparaffinic.
14. Use according to claim 13, wherein the isoparaffin is reacted with oxygen at a temperature below 250 ℃.
15. Use according to claim 13, wherein the isoparaffin is reacted with oxygen at a temperature in the range of 80-200 ℃.
16. Use according to claim 13, wherein the isoparaffin is reacted with oxygen at a temperature in the range of 80-150 ℃.
17. Use according to claim 13, characterized in that the isoparaffin oxidation time is between 10min and 10h.
18. Use according to claim 13, characterized in that the isoparaffin oxidation time is between 30min and 6h.
19. The use according to claim 9, wherein the isoparaffin comprises an isoparaffin having a C7 or lower content.
20. Use according to claim 9, characterized in that the isoparaffin is isobutane.
21. The use according to claim 9, wherein the reaction temperature is controlled in the range of 90-300 ℃.
22. Use according to claim 9, characterized in that the reaction temperature is controlled in the range of 90-200 ℃.
23. The use according to claim 9, wherein the contact reaction time of isoparaffin hydrogen peroxide with the catalyst is in the range of 0.5s to 10s.
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CN101541745A (en) * 2006-09-28 2009-09-23 波利玛利欧洲股份公司 Process for the preparation of phenol by means of new catalytic systems
CN102173977A (en) * 2011-03-10 2011-09-07 江苏大学 Cu/Al2O3 catalyst and preparation method thereof as well as method for catalyzing hydrolysis of glycerol
CN102548936A (en) * 2009-06-29 2012-07-04 波利玛利欧洲股份公司 Process for the preparation of phenol and cyclohexanone
CN102807481A (en) * 2012-08-22 2012-12-05 山东科技大学 Method for preparing methyl ethyl ketone by oxidizing normal butane
CN111111670A (en) * 2019-12-05 2020-05-08 华茂伟业绿色科技股份有限公司 Supported catalyst and preparation method and application thereof
CN111514940A (en) * 2019-02-02 2020-08-11 中国科学院大连化学物理研究所 Catalyst for one-step preparation of acetone, preparation method and application thereof

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WO2018111960A1 (en) * 2016-12-14 2018-06-21 Exxonmobil Research And Engineering Company Production of high octane hydrocarbon from isobutane via tert-butanol

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Publication number Priority date Publication date Assignee Title
CN1403431A (en) * 2001-09-05 2003-03-19 中国科学院大连化学物理研究所 Catalyst for preparing methoxy acetone and its prepn and application
CN101541745A (en) * 2006-09-28 2009-09-23 波利玛利欧洲股份公司 Process for the preparation of phenol by means of new catalytic systems
CN102548936A (en) * 2009-06-29 2012-07-04 波利玛利欧洲股份公司 Process for the preparation of phenol and cyclohexanone
CN102173977A (en) * 2011-03-10 2011-09-07 江苏大学 Cu/Al2O3 catalyst and preparation method thereof as well as method for catalyzing hydrolysis of glycerol
CN102807481A (en) * 2012-08-22 2012-12-05 山东科技大学 Method for preparing methyl ethyl ketone by oxidizing normal butane
CN111514940A (en) * 2019-02-02 2020-08-11 中国科学院大连化学物理研究所 Catalyst for one-step preparation of acetone, preparation method and application thereof
CN111111670A (en) * 2019-12-05 2020-05-08 华茂伟业绿色科技股份有限公司 Supported catalyst and preparation method and application thereof

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