CN115106115A - Method for preparing acetone from alkane - Google Patents

Method for preparing acetone from alkane Download PDF

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CN115106115A
CN115106115A CN202110294136.8A CN202110294136A CN115106115A CN 115106115 A CN115106115 A CN 115106115A CN 202110294136 A CN202110294136 A CN 202110294136A CN 115106115 A CN115106115 A CN 115106115A
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catalyst
molecular sieve
usy
acetone
reaction
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CN115106115B (en
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李春义
李宁
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China University of Petroleum East China
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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
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    • 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
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    • 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
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    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
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    • 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
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    • 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
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    • C07C407/00—Preparation of peroxy compounds
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    • 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 of preparing acetone, comprising: the isoalkane hydrogen peroxide is decomposed under the action of a catalyst to generate acetone and alcohol substances; the catalyst comprises an active component and a carrier, wherein the active component comprises a metal element and/or a zeolite molecular sieve, and the metal element comprises Ce, Ti, Zr, Nb, W, V, Cr, Mo, Mn, Co, Fe, Cu, Ni, Zn and Ag elements; the zeolite molecular sieve comprises one or more of Y-type molecular sieve, USY-type molecular sieve, ZSM-5 type molecular sieve, beta-type molecular sieve, mordenite and offretite. The hydrogen peroxide of isoparaffin is prepared by oxidizing isoparaffin, and the cost is low.

Description

Method for preparing acetone from alkane
Technical Field
The invention 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 and 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 used for producing other solvents.
The production method of acetone mainly comprises a fermentation method, an organic matter hydration method, a propylene oxidation method, an isobutyraldehyde oxidation method and the like.
The earliest production method of acetone is a fermentation method, which takes grains or other saccharides as raw materials, obtains sterile fermentation base liquid after high-temperature cooking sterilization, then adds specific strains for fermentation, and obtains the acetone after the liquid after fermentation is distilled. The fermentation method has the disadvantages of laggard technology, high production cost and low efficiency, and the method is basically eliminated at present.
The propylene oxidation method takes oxygen as an oxidant to oxidize propylene into acetone, takes a catalyst with copper chloride-palladium chloride as an active component to catalyze the propylene to be oxidized into acetone, and can realize the recycling regeneration of the catalyst through the following reaction. First, propylene reacts with PdCl 2 Reduction to Pd, simultaneous generation of acetone and HCl, reoxidation of Pd to PdCl by another component of CuCl2 on the catalyst 2 And CuCl 2 Is reduced to CuCl and finally CuCl is added in HCl and O 2 Re-oxidized to CuCl2, thereby completing the cycle.
Figure BDA0002983667540000011
Pd+2CuCl 2 →PdCl 2 +2CuCl
2CuCl+1/2O 2 +2HCl→2CuCl 2 +H 2 O
This method has a high acetone yield but is difficult to apply industrially because of the price of isobutyraldehyde, which is a reaction raw material.
The current major production process for acetone is cumene oxidation, the major technology licensed companies of this process are KBR, mitsui, japan and UOP in the united states. The method mainly comprises the production steps of cumene synthesis, cumene peroxidation, cumene hydroperoxide concentration, decomposition and neutralization, product refining and the like. It is reported in literature that when cumene peroxide is used as a raw material, the temperature of a reactor gradually increases along with the flow direction of the raw material, a mixture of the cumene peroxide and the dicumyl peroxide is firstly generated under the catalytic action of concentrated sulfuric acid, then the dicumyl peroxide is decomposed into a mixed solution of acetone and phenol by increasing the reaction temperature, and the product phenol and acetone are obtained by a method such as rectification. Or, using the mixed solution of cumyl peroxide and cumyl as raw material, firstly, the reaction temperature is 40-75 ℃, under the catalytic action of organic acid, such as 2-hydroxy-5-methyl-benzene sulfonic acid, 4-hydroxybenzene-1, 3-disulfonic acid, 2-hydroxy-5-methoxybenzene sulfonic acid and the like, the mixed solution of dicumyl peroxide and cumyl is generated, then, 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 process requires a large amount of acid and the reacted mixture needs to be neutralized by adding an excess amount of acid before purification.
Or cumene can be used as a raw material, and part of the cumene can be oxidized into the cumene hydroperoxide in the presence of oxygen to obtain a mixture of the cumene hydroperoxide and the cumene. The mixed liquid contacts a non-acidic catalyst, and part of the cumyl peroxide and the unreacted cumyl in the mixed liquid generate the dimethylbenzyl methanol. The solution containing dimethylbenzyl alcohol is contacted with an acidic 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 simultaneously reduces the production cost.
The acetone produced by the isopropyl benzene method has the advantages of high product quality, low raw material and energy consumption and the like, but 2 tons of phenol are produced in a co-production mode when 1 ton of acetone is produced, and the economic benefit of the acetone production by the method is more easily restricted by the supply and demand relationship of the phenol market.
Other methods for producing acetone, such as fermentation, dehydrogenation of isopropyl alcohol, oxidation of propylene, hydration of acetylene and acetic acid by-production, are difficult to apply because of limitations in production efficiency or production cost.
The present invention is therefore specified.
Disclosure of Invention
The invention aims to reduce the production cost of acetone and improve the production efficiency.
The invention also aims to provide a catalyst for preparing acetone from isoparaffin hydrogen peroxide.
In order to realize the purpose, the following technical scheme is adopted:
a method of preparing acetone, comprising: the isoalkane hydrogen peroxide is decomposed under the action of a catalyst to generate acetone and alcohol substances.
Figure BDA0002983667540000031
The isoparaffin hydrogen peroxide can be prepared by oxidizing isoparaffin serving as a raw material, the raw material has low cost, and some byproducts can be used as important components of fuel liquefied gas.
Detailed Description
The process for the preparation of acetone according to the present application is described in further detail below. And do not limit the scope of the present application, which is defined by the claims. Certain disclosed specific details provide a thorough understanding of various disclosed embodiments. One skilled in the relevant art will recognize, however, that embodiments may be practiced without one or more of the specific details, with other materials, etc.
Unless the context requires otherwise, in the description and claims, the terms "comprise," comprises, "and" comprising "are to be construed in an open-ended, inclusive sense, i.e., as" including, but not limited to.
In the present specification, the numerical range represented by "a numerical value a to B numerical value B" means a range including the end point numerical value A, B.
In the present specification, the numerical ranges indicated by "above" or "below" mean the numerical ranges including the present numbers.
Reference in the specification to "an embodiment," "one embodiment/preferred embodiment," "another embodiment/preferred embodiment," or "certain embodiments," etc., means that a particular element (e.g., feature, structure, or characteristic) described in connection with the embodiment is included in at least one embodiment. Thus, "an embodiment," "another embodiment," or "certain embodiments" do not necessarily all refer to the same embodiments. Furthermore, the particular features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. Each feature disclosed in this specification may be replaced by an alternative feature serving the same, equivalent, or similar purpose. Thus, unless expressly stated otherwise, the features disclosed are merely generic examples of equivalent or similar features.
The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out according to conventional conditions or according to conditions recommended by the manufacturers. All percentages, ratios, proportions, or parts are by weight unless otherwise specified.
Defining:
the structural feature of isoparaffins herein refers to methyl substituents in the 2-position, i.e., 2-methyl alkanes.
In the specification, the term "Cn isomerized alkane" means that the total number of carbon atoms in the isomerized alkane is n. The isomerized alkane having not more than C10 means that the total number of carbon atoms of the isomerized alkane is not more than 10.
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 embodiments and materials described herein are intended to be exemplary only.
In one aspectThe catalyst for preparing acetone from isoparaffin comprises 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 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 40 wt%, preferably 0.3 to 20 wt%. The weight of the metal element is calculated as the highest valent oxide.
The metal element may be present in the form of a metal or may be a metal oxide, 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 of the catalyst is 5-80 wt%, preferably 20-50 wt%.
In certain embodiments, the zeolitic molecular sieve, preferably one of the USY, ZSM-5 and beta types, 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 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 some embodiments, in the catalyst for preparing acetone from isoparaffin, the active component is selected from USY molecular sieve or beta type molecular sieve. The yield of acetone is better.
The preparation method of the catalyst can adopt the preparation commonly used in the prior art, such as adopting a method of firstly pulping and then spraying for granulation; or the product can be made by a method of extruding after kneading; the rolling ball method and the like can also be used.
In one embodiment, a method of preparing a catalyst comprises: mixing the material containing metal element and molecular sieve with the sol containing carrier component, drying and roasting to obtain the catalyst.
In some embodiments, the preparation method of the catalyst comprises the steps of firstly loading the metal elements on the zeolite molecular sieve by an impregnation method, mixing the obtained loaded zeolite molecular sieve with a sol containing a carrier component, drying and roasting to obtain the catalyst.
On the other hand, in the case of a system,a method of preparing acetone, comprising: the isoalkane hydrogen peroxide is decomposed under the action of a catalyst to generate acetone and alcohol substances. The above-mentioned catalyst is used in the course of the reaction.
In certain embodiments, the isoparaffins include C10 and lower isoparaffins. Preferably, isomerized alkanes of C7 or less; isobutane is more preferred.
In the application, the isoparaffin hydrogen peroxide is reacted under the action of a catalyst to generate acetone under the condition that the reaction temperature is controlled within the range of 50-350 ℃. The reaction temperature is preferably controlled in the range of 90 to 300 ℃.
In certain embodiments, the isoparaffin hydrogen peroxide is reacted with the catalyst to form acetone at a reaction temperature controlled in the range of 60-200 ℃.
In some embodiments, the contact reaction time of the isoparaffin hydrogen peroxide and the catalyst is controlled within 0.1s-2min, preferably within 0.5s-10 s.
The catalytic decomposition reaction of the isoparaffin hydrogen peroxide is carried out in a fixed bed, and the average residence time in the catalyst bed layer calculated by the apparent gas velocity is 0.1s-2min, preferably 0.5s-10 s.
For the reactants which are liquid at normal temperature and normal pressure, the reactants enter a fixed bed of the reactor to react after being preheated into gas.
In the present application, isoparaffin hydrogen peroxide is converted to acetone and the corresponding alcohol in a short time at a temperature below 200 ℃ by contacting with the catalyst.
When iso-alkane hydrogen peroxide is selected as iso-butane hydrogen peroxide, the yield of acetone is more than 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 present 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 of 80 to 200 ℃.
In certain embodiments, the isoparaffin is reacted with oxygen at a temperature in the range of 80 to 150 ℃.
The alkane oxidation time is preferably 10min-10h, preferably 30min-6 h.
Under the above reaction conditions, safety can be ensured and operation outside the explosive limit is required. That is, during the isoparaffin peroxidation, the oxygen concentration is mainly controlled at a low level to keep the reaction mixture away from the explosion limit range for 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 process for preparing acetone in the prior art, the acetone preparation method at least comprises the following advantages:
1) the raw material for preparing acetone, namely isoparaffin, has wide sources and low price. Therefore, the prepared acetone selects low-cost iso-paraffins such as isobutane as raw materials, and the price fluctuation is small. The alcohol substance as a by-product of the reaction is not limited to small molecular alcohols such as methanol and ethanol, but also large molecular alcohols such as propanol, butanol and pentanol, and has a wide range of applications.
2) In the whole preparation process, the temperature is below 350 ℃, so that the preparation method is mild, simple in process, low in energy consumption and high in efficiency. The two-step reaction can be completed in two reactors, and the reaction is exothermic, so that not only is complex heat supply equipment not required, but also heat can be taken from the reaction to be used as a heat source in the subsequent separation process, and the fuel consumption is low and the energy consumption is low.
3) Low-value by-products yield is low, and economic benefit is good. In the case of t-butane, the desired product of the reaction is acetone, and the major by-products are t-butanol, methanol and isobutylene, which are all starting materials for the production of MTBE. CO, CO 2 And few by-products such as methane and water.
The method for preparing acetone and the technical effects obtained by the method are further described by using specific examples.
Example 1
Taking a certain amount of silica Sol (SiO) 2 Calculated by mass percent of 30 percent) is placed in a stirring kettle for stirring, a certain amount of ZSM molecular sieve is added (the mass percent of ZSM in the finally obtained catalyst is 30 percent), the mixture is continuously stirred for 2 hours, dried at 120 ℃, roasted at 700 ℃ for 2 hours, and then the 30 percent ZSM/SiO is obtained 2 A catalyst.
Example 2
Taking a certain amount of silica Sol (SiO) 2 Calculated by mass percent of 30 percent) is placed in a stirring kettle to be stirred, a certain amount of USY molecular sieve is added (the mass percent of the USY molecular sieve in the finally obtained catalyst is 30 percent), the mixture is continuously stirred for 2 hours, dried at 120 ℃, roasted at 700 ℃ for 2 hours, and then 30 percent USY/SiO is obtained 2 A catalyst.
Example 3
Taking a certain amount of silica Sol (SiO) 2 Calculated by mass percent of 30 percent) is placed in a stirring kettle to be stirred, a certain amount of H beta molecular sieve is added (the mass percent of the H beta molecular sieve in the finally obtained catalyst is 30 percent), the mixture is continuously stirred for 2 hours, dried at 120 ℃, roasted at 700 ℃ for 2 hours, and then 30 percent H beta/SiO is obtained 2 A catalyst.
Example 4
Taking a certain amount of silica Sol (SiO) 2 Calculated by mass fraction of 30 percent) is placed in a stirrerStirring in a kettle, adding a certain amount of MCM-41 molecular sieve (the mass fraction of the MCM-41 molecular sieve in the finally obtained catalyst is 30%), continuously stirring for 2h, drying at 120 ℃, roasting at 700 ℃ for 2h to obtain 30% MCM-41/SiO 2 A catalyst.
Example 5
Taking a certain amount of USY molecular sieve catalyst, and soaking a certain amount of ammonium metatungstate solution (so that WO is enabled) 3 Accounting for 10 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain WO 3 -USY. Taking a certain amount of silica Sol (SiO) 2 Calculated by mass fraction of 30 percent) is placed in a stirring kettle for stirring, and a certain amount of WO is added 3 Continuing stirring for 2h, drying at 120 ℃ and roasting at 700 ℃ for 2h to obtain 10% WO (tungsten trioxide) Y (so that the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), and obtaining WO 3 -30％USY/SiO 2 A catalyst.
Example 6
Soaking a certain amount of USY molecular sieve catalyst into a certain amount of ammonium molybdate solution (so that MoO is generated) 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 silica Sol (SiO) 2 Calculated by mass fraction of 30 percent) is placed in a stirring kettle for stirring, and a certain amount of MoO is added 3 Continuing stirring for 2h, drying at 120 ℃ and roasting at 700 ℃ for 2h to obtain 10% MoO (molybdenum oxide) USY (the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), and then 3 -30％USY/SiO 2 A catalyst.
Example 7
And (3) taking a certain amount of USY molecular sieve catalyst, soaking a certain amount of cobalt nitrate solution (enabling CoO to account for 10% of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain CoO-USY. Taking a certain amount of silica Sol (SiO) 2 Calculated by mass percent of 30 percent) is placed in a stirring kettle for stirring, a certain amount of CoO-USY (the mass percent of the USY molecular sieve in the finally obtained catalyst is 30 percent) is added, the mixture is continuously stirred for 2 hours, and then is dried at 120 ℃ and roasted at 700 ℃ for 2 hours, thus obtaining 10 percent CoO-30 percent USY/SiO 2 A catalyst.
Example 8
And (3) soaking a certain amount of USY molecular sieve catalyst into a certain amount of nickel nitrate solution (the NiO accounts for 10% of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2h to obtain NiO-USY. Taking a certain amount of silica Sol (SiO) 2 Calculated by mass percent of 30 percent) is placed in a stirring kettle to be stirred, a certain amount of NiO-USY (the mass percent of the USY molecular sieve in the finally obtained catalyst is 30 percent) is added, the mixture is continuously stirred for 2 hours, dried at 120 ℃, roasted at 700 ℃ for 2 hours, and then 10 percent NiO-30 percent USY/SiO are obtained 2 A catalyst.
Example 9
Taking a certain amount of silica Sol (SiO) 2 Calculated by mass fraction of 30 percent), adding a certain amount of USY molecular sieve for pulping (accounting for 30 percent of the total mass of the catalyst), and then adding a certain amount of titanyl sulfate (taking TiO as raw material) 2 Accounting for 10 percent of the total mass of the catalyst), evenly stirring and then carrying out spray granulation. The obtained solid microspheres are roasted for 2 hours at 700 ℃, and 10 percent TiO can be obtained 2 -30％USY/SiO 2 A catalyst.
Example 10
Soaking a certain amount of USY molecular sieve catalyst in a certain amount of ferric nitrate solution (to make Fe 2 O 3 Accounting for 10 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain Fe 2 O 3 -USY. Taking a certain amount of silica Sol (SiO) 2 Calculated by 30 percent) of the weight percent, adding a certain amount of Fe 2 O 3 Pulping USY molecular sieve (making USY account for 30% of the total mass of the catalyst), uniformly stirring, and then carrying out spray granulation. The obtained solid microspheres are roasted for 2 hours at 700 ℃, and then 10 percent Fe can be obtained 2 O 3 -30％USY/SiO 2 A catalyst.
Example 11
Soaking certain amount of USY molecular sieve catalyst in certain amount of ammonium metatungstate 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 WO 3 -MoO 3 -USY. Taking a certain amount of silica Sol (SiO) 2 Calculated by 30 percent of mass percent) is added with a certain amount of WO 3 -MoO 3 -UAnd pulping the SY molecular sieve (the USY accounts for 30 percent of the total mass of the catalyst), uniformly stirring, and then carrying out spray granulation. The obtained solid microspheres are roasted for 2 hours at 700 ℃, and 5 percent of WO can be obtained 3 -5％MoO 3 -30％USY/SiO 2 A catalyst.
Example 12
Soaking a certain amount of USY molecular sieve in a certain amount of ammonium metatungstate and ferric nitrate solution (so that WO is obtained) 3 And 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 WO 3 -Fe 2 O 3 -USY. Taking a certain amount of silica Sol (SiO) 2 Calculated by mass fraction of 30 percent) is put into a beaker and stirred, and a certain amount of WO is added 3 -Fe 2 O 3 Continuing stirring for 2h, drying at 120 ℃ and roasting at 700 ℃ for 2h to obtain 5% WO (tungsten trioxide) (USY) (the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), and obtaining the final product 3 -5％Fe 2 O 3 -30％USY/SiO 2 A catalyst.
Example 13
Taking a certain amount of silica Sol (SiO) 2 Calculated by mass percent of 30 percent), adding a certain amount of USY molecular sieve for pulping (accounting for 30 percent of the total mass of the catalyst), and adding a certain amount of ammonium molybdate and ferric nitrate solution (so as to ensure MoO) 3 And Fe 2 O 3 Each accounting for 5 percent of the total mass of the catalyst) and then spray granulation is carried out after uniform stirring. The obtained solid microspheres are roasted for 2h at 700 ℃, dried at 120 ℃ and roasted for 2h at 700 ℃ to obtain 5 percent MoO 3 -5％Fe 2 O 3 -30％USY/SiO 2 A catalyst.
Example 14
Putting a certain amount of alumina sol into a stirring kettle for stirring, adding a certain amount of ZSM molecular sieve (ensuring that the ZSM mass fraction in the finally obtained catalyst is 30%), continuing stirring for 2h, drying at 120 ℃, roasting at 700 ℃ for 2h to obtain 30% ZSM/Al 2 O 3 A catalyst.
Example 15
Putting a certain amount of alumina sol into a stirring kettle for stirring, and then adding a certain amount of H beta molecular sieve (so as to finally obtain the catalystThe mass fraction of the intermediate H beta is 30 percent), continuously stirring for 2 hours, drying at 120 ℃, roasting at 700 ℃ for 2 hours to obtain 30 percent H beta/Al 2 O 3 A catalyst.
Example 16
Putting a certain amount of aluminum sol into a stirring kettle, stirring, adding a certain amount of USY molecular sieve (the mass fraction of USY in the finally obtained catalyst is 30%), continuing stirring for 2h, drying at 120 ℃, roasting at 700 ℃ for 2h to obtain 30% USY/Al 2 O 3 A catalyst.
Example 17
Taking a certain amount of USY molecular sieve catalyst, and soaking a certain amount of ammonium metatungstate solution (so that WO is generated) 3 Accounting for 10 percent of the total mass of the catalyst), drying at 120 ℃, and roasting at 550 ℃ for 2 hours to obtain WO 3 -USY. Taking a certain amount of aluminum sol and a certain amount of WO 3 And (3) uniformly mixing the USY (the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), kneading and extruding. Obtaining a long-strip catalyst, roasting at 700 ℃ for 2h to obtain 10 percent WO 3 -30％USY/Al 2 O 3 A catalyst.
Example 18
Soaking a certain amount of USY molecular sieve catalyst into a certain amount of ammonium molybdate solution (so that MoO is generated) 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 alumina sol and a certain amount of MoO 3 And (3) uniformly mixing the USY (the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), kneading and extruding. Obtaining a long-strip catalyst, roasting at 700 ℃ for 2h to obtain 10% MoO 3 -30％USY/Al 2 O 3 A catalyst.
Example 19
Taking a certain amount of USY molecular sieve catalyst, fully mixing with a certain amount of aluminum sol (the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), and adding a certain amount of ferric nitrate (the mass fraction of Fe is enabled to be Fe) into the mixture 2 O 3 Accounting for 10 percent of the total mass of the catalyst), uniformly mixing, kneading and extruding. Obtaining a long-strip catalyst, roasting the catalyst for 2 hours at 700 ℃,then 10% Fe can be obtained 2 O 3 -30％USY/Al 2 O 3 A catalyst.
Example 20
Taking a certain amount of USY molecular sieve catalyst, and soaking a certain amount of ammonium metatungstate and ferric nitrate solution (so that WO is enabled) 3 And 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 WO 3 -Fe 2 O 3 -USY. Taking a certain amount of pseudoboehmite and a certain amount of WO 3 -Fe 2 O 3 USY (the mass fraction of USY molecular sieve in the finally obtained catalyst is 30%) is uniformly mixed, and a certain amount of water rolling balls are added. Obtaining a spherical catalyst, roasting at 700 ℃ for 2h to obtain 5 percent WO 3 -5％Fe 2 O 3 -30％USY/Al 2 O 3 A catalyst.
Example 21
Taking a certain amount of USY molecular sieve catalyst, fully mixing with a certain amount of pseudo-boehmite (the mass fraction of the USY molecular sieve in the finally obtained catalyst is 30%), adding a certain amount of ammonium molybdate solution (the MoO is enabled to be in a certain range) 3 5 percent of the total mass of the catalyst), and then adding a certain amount of ferric nitrate solution (to ensure that Fe is contained 2 O 3 Each accounting for 5 percent of the total mass of the catalyst) and rolling balls after uniform mixing. Obtaining a spherical catalyst, roasting at 700 ℃ for 2h to obtain 5 percent MoO 3 -5％Fe 2 O 3 -30％USY/Al 2 O 3 A catalyst.
Example 22
Preparation of isobutane hydroperoxide:
the peroxidation of the isobutane takes the isobutane and oxygen as raw materials, the introduction amount of the oxygen is calculated according to the maximum conversion rate of the isobutane, the reaction temperature is 120 ℃, the retention time is 2 hours, and the reaction pressure is 2.8 Mpa. The results are shown in Table 1.
Example 23
Preparation of isobutane hydroperoxide:
the peroxidation of the isobutane takes the isobutane and oxygen as raw materials, the introduction amount of the oxygen is calculated according to the maximum conversion rate of the isobutane, the reaction temperature is 140 ℃, the retention time is 2 hours, and the reaction pressure is 3.6 Mpa. The results are shown in Table 1.
Peroxidation of isopentane the experimental results for the preparation of isopentyl hydroperoxide are shown in examples 3-4.
Example 24
Preparation of isopentane hydroperoxide:
the peroxidation of the isopentane takes the isopentane and oxygen as raw materials, the introduction amount of the oxygen is calculated according to the maximum conversion rate of the isopentane of 20 percent, the reaction temperature is 120 ℃, the retention time is 2 hours, and the reaction pressure is 1.02 Mpa. The results are shown in Table 2.
Example 25
Preparation of isopentane hydroperoxide:
the peroxidation of the isopentane takes isopentane and oxygen as raw materials, the introduction amount of the oxygen is calculated according to the maximum conversion rate of the isopentane of 20 percent, the reaction temperature is 140 ℃, the retention time is 2 hours, and the reaction pressure is 1.5 Mpa. The results are shown in Table 2.
The products obtained in examples 22 to 23 were subjected to separation purification using t-butyl hydroperoxide as shown in Table 1. The products obtained in examples 24-25 were subjected to separation and purification of isoamyl hydroperoxide as shown in Table 2.
TABLE 1
Figure BDA0002983667540000111
TABLE 2
Figure BDA0002983667540000112
The isoamyl hydroperoxide or t-butyl hydroperoxide obtained in examples 22 to 25 was subjected to the following catalytic decomposition reaction. As the reaction results of the reactant tert-butyl hydroperoxide shown in the data of Table 3, the catalysts prepared in examples 1-21 were selected respectively during the reaction at 140 ℃ for a residence time of 7 s. Residence time in this application is understood to mean the contact time of the catalyst with the alkyl hydroperoxide.
The catalysts of examples 1-21 can also be used to catalyze the decomposition of isoamyl hydroperoxide or t-butyl hydroperoxide.
Example 26
Using the catalyst of example 19 and isoamyl hydroperoxide as the starting material, the reaction conditions were the same, the reaction temperature was 140 ℃ and the residence time was 7 seconds, and the reaction results are shown in Table 4.
Example 27
Using isopentyl hydroperoxide as the starting material and the catalyst of example 20, the reaction conditions were the same as those of example 26, and the results are shown in Table 4.
Example 28
Using isopentyl hydroperoxide as a starting material and the catalyst of example 21, the reaction conditions were the same as those of example 26, and the results are shown in Table 4.
Example 29
Preparation of MoO 3 /Al 2 O 3 Catalyst, taking a certain amount of Al 2 O 3 After the water absorption was measured, Al was immersed in a predetermined amount of ammonium heptamolybdate solution 2 O 3 On a carrier (in MoO) 3 The loading amount is 10 wt%), after the impregnation is finished, drying at 120 ℃, and roasting at 700 ℃ for 2h to obtain MoO 3 /Al 2 O 3 A catalyst.
MoO prepared by using tert-butyl hydroperoxide as raw material in a fixed bed reactor 3 /Al 2 O 3 The catalyst is prepared by taking the reaction solution as a catalyst, keeping the reaction temperature at 130 ℃ for 7s, and stabilizing the reaction solution for 1h after the raw materials are introduced for sampling and analysis.
With the exception of this example, examples 30-33 all used this catalyst at 10 wt% MoO 3 /Al 2 O 3 。
Example 30
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, and MoO is used 3 /Al 2 O 3 The catalyst is prepared by the steps of reacting at 140 ℃ for 7s, and stabilizing for 1h after raw materials are introduced for sampling analysis.
Example 31
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, and MoO is used 3 /Al 2 O 3 The catalyst is prepared by the steps of reacting at the temperature of 150 ℃ for 7s, introducing the raw materials, stabilizing for 1h, and sampling and analyzing.
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 is 130 ℃, the retention time is 27s, and the sampling analysis is carried out after the raw materials are stabilized for 1 h.
Example 33
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, and MoO is used 3 /Al 2 O 3 The catalyst is prepared by taking samples and analyzing after the reaction temperature is 130 ℃, the retention time is 54s and the raw materials are stabilized for 1 h.
Experiments of the reaction conditions are shown in comparative examples 4-5 and examples 29-33, and the results are listed in Table 5.
Comparative example 1
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, quartz sand is filled in the reactor as a catalyst, the reaction temperature is 140 ℃, the residence time of the reaction raw material in a bed layer is 7s, and the sample is taken for analysis after the reaction raw material is introduced and stabilized for 1h, as shown in Table 1.
Comparative example 2
In a fixed bed reactor, taking tert-butyl hydroperoxide as a raw material, and filling SiO in the reactor 2 As a catalyst, the reaction temperature was 140 ℃, the residence time of the reaction raw material in the bed was 7s, and the sample was taken for 1h after the raw material was introduced, as shown in Table 1.
Comparative example 3
In a fixed bed reactor, taking an aqueous solution of tert-butyl hydroperoxide as a raw material, and filling Al in the reactor 2 O 3 As a catalyst, the reaction temperature was 140 ℃, the residence time of the reaction raw material in the bed was 7s, and the sample was taken for 1h after the introduction of the raw material and analyzed as shown in Table 1.
Comparative example 4
In the fixed-penetration reactor, the reaction solution is,using tert-butyl hydroperoxide as raw material and MoO 3 /Al 2 O 3 The catalyst is prepared by the steps of reacting at 40 ℃ for 7s, and stabilizing for 1h after raw materials are introduced for sampling analysis.
Comparative example 5
In a fixed bed reactor, tert-butyl hydroperoxide is used as a raw material, and MoO is used 3 /Al 2 O 3 As a catalyst, the reaction temperature is 130 ℃, the retention time is 0.05s, and the sample is taken for analysis after the raw materials are led in and stabilized for 1 h.
TABLE 3
Figure BDA0002983667540000141
TABLE 4
Figure BDA0002983667540000151
TABLE 5
Figure BDA0002983667540000152

Claims (10)

1. A catalyst for preparing acetone from isoalkane comprises 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 of Y-type molecular sieve, USY-type molecular sieve, ZSM-5 type molecular sieve, beta-type molecular sieve, mordenite and offretite;
preferably, the active component metal element in the catalyst comprises WO 3 、TiO 2 、MnO x 、MoO x 、CoO x 、FeO x 、CuO x One or more of them.
2. The catalyst according to claim 1, wherein the metal element is present in the catalyst in an amount of 0.1-40 wt.%, preferably 0.3-20 wt.%, calculated as the highest oxide.
3. A catalyst according to claim 1 or 2, wherein the zeolite molecular sieve is present in the catalyst in an amount of from 5% to 80% by weight, preferably from 20% to 50% by weight.
4. A catalyst according to any one of claims 1 to 3, wherein the zeolite molecular sieve is preferably one of USY, ZSM-5 and beta type molecular sieves.
5. A catalyst according to any one of claims 1 to 3, characterized in that the carrier comprises Al 2 O 3 、SiO 2 Kaolin, diatomaceous earth, MgO, CaO and La 2 O 3 Preferably Al 2 O 3 、SiO 2 And kaolin, or a mixture of both.
6. A method of preparing acetone, comprising: the isoalkane hydrogen peroxide is decomposed to generate acetone and alcohol substances under the action of the catalyst of any one of claims 1 to 4;
preferably, the isoparaffins include isomerized alkanes of C10 or less; preferably, isomerized alkanes of C7 or less; isobutane is more preferred.
7. The preparation method of claim 6, wherein the isoparaffin hydrogen peroxide is reacted under the action of the catalyst to generate acetone at the reaction temperature controlled within the range of 50-350 ℃;
the preferable reaction temperature is controlled in the range of 90-300 ℃;
preferably, the reaction temperature is controlled in the range of 90-200 ℃.
8. The process according to claim 6 or 7, wherein the contact reaction time of the isoparaffin hydrogen peroxide with the catalyst is 0.1s-2min, preferably 0.5s-10 s.
9. The process according to claim 6 or 7, wherein the catalytic decomposition reaction of the isoalkane hydroperoxide is carried out in a fixed bed, and the mean residence time in the catalyst bed is 0.1s-2min, preferably 0.5s-10s, calculated from the superficial gas velocity.
10. The process according to any one of claims 6 to 10, wherein the isoparaffin hydrogen peroxide is produced by oxidizing isoparaffin;
preferably, the isoparaffin is reacted with oxygen at a temperature below 250 ℃;
preferably, the reaction is carried out at a temperature ranging from 80 to 200 ℃; more preferably, the reaction is carried out at a temperature ranging from 80 to 150 ℃;
preferably, the alkane oxidation time is preferably between 10min and 10h, preferably between 30min and 6 h.
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CN102807481A (en) * 2012-08-22 2012-12-05 山东科技大学 Method for preparing methyl ethyl ketone by oxidizing normal butane
US20180162789A1 (en) * 2016-12-14 2018-06-14 Exxonmobil Research And Engineering Company Methods and systems for converting hydrocarbons
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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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
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