CN111018651A - Method for preparing aromatic hydrocarbon from light hydrocarbon at low temperature - Google Patents

Method for preparing aromatic hydrocarbon from light hydrocarbon at low temperature Download PDF

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Publication number
CN111018651A
CN111018651A CN201911280927.4A CN201911280927A CN111018651A CN 111018651 A CN111018651 A CN 111018651A CN 201911280927 A CN201911280927 A CN 201911280927A CN 111018651 A CN111018651 A CN 111018651A
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ionic liquid
light hydrocarbon
aromatic hydrocarbon
catalyst
reaction
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白正帅
邓紫琴
雷丽
王廷海
岳源源
袁珮
朱海波
崔勍焱
鲍晓军
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Fuzhou University
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Fuzhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/367—Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
    • C07C5/393—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation with cyclisation to an aromatic six-membered ring, e.g. dehydrogenation of n-hexane to benzene
    • C07C5/41—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/025—Sulfonic acids
    • 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

Abstract

The invention discloses a method for preparing aromatic hydrocarbon by light hydrocarbon at low temperature. The invention uses the ionic liquid as the catalyst, and carries out aromatization reaction on light hydrocarbon under the atmosphere of nitrogen or hydrogen to obtain an aromatization product. The invention utilizes the characteristic of high activity of the ionic liquid at low temperature, and applies the ionic liquid to light hydrocarbon aromatization reaction for the first time, which has very important significance and use value for the development of low-temperature aromatization technology.

Description

Method for preparing aromatic hydrocarbon from light hydrocarbon at low temperature
Technical Field
The invention belongs to the field of petrochemical industry, and particularly relates to a method for preparing aromatic hydrocarbon at low temperature by using light hydrocarbon.
Background
BTX aromatics are commonly referred to as Benzene (B), Toluene (T), and Xylene (X). The most important purpose of the gasoline is to serve as an important basic chemical raw material and also serve as a common gasoline blending component of a gasoline octane number. In recent years, the demand of aromatic hydrocarbon is rapidly increased, but the development of domestic productivity and yield is seriously delayed, the productivity and yield of basic aromatic hydrocarbon are improved, and the research and development of aromatic hydrocarbon yield increasing technology are accelerated. The light hydrocarbon aromatization technology generally refers to a technology for preparing aromatic hydrocarbon by carrying out composite reaction steps of dehydrogenation, cracking, oligomerization, hydrogen transfer, cyclization, isomerization and the like on small molecular hydrocarbons under the action of a catalyst. The key to this technology is the development of catalysts.
In the prior documents and patents, the catalyst used in the light hydrocarbon aromatization technology is generally a solid catalyst such as a molecular sieve. Such as Mole et al (Mole T, Anderson J R. The interaction of propane over ZSM-5-H and ZSM-5-Zn zeolite catalysts [ J]Applied Catalysis, 1985, 17(1): 141-154.) the conversion of propane was 35% and the selectivity to aromatics was about 63% using Zn/HZSM-5 as catalyst, but 773K was required for the reaction temperature. Preparation and reaction research of Wanhai et al (Wanhai. novel L zeolite-based light hydrocarbon aromatization catalyst [ D)]2015.) Ga prepared in grades1.0-ZSM-5/Pt0.6the-L composite molecular sieve is used as a catalyst, and compared with the existing industrial catalyst, the catalytic result improves the conversion rate of raw materials by 4.6%, the yield of aromatic hydrocarbon by 5.9%, the yield of p-xylene by 7.3%, but the reaction temperature needs 793K. Although these catalysts have good activity, most of them need to be maintained at a high temperatureThe catalyst is operated under hydrogen atmosphere, but the high-temperature reaction condition easily causes the loss of active metal components, thereby causing the reduction of catalytic activity and having the defects of high energy consumption and high cost. Therefore, development of a low-temperature and low-consumption aromatization catalyst is a development trend of future aromatization technology.
Ionic liquids have a wide and promising range of applications due to their numerous enhanced properties. L-acidic ionic liquids are currently commonly used in alkane alkylation reactions (Hu P, Wang Y, Meng X, et al, Isobutane alkylation with 2-branched alkyl by amide-AlCl3-based ionic liquids [ J ]. Fuel,2017, 189:203 @) and isomerization reactions (Meyer C, Wasseracid P. Effective n-aliphatic isomerization and excess mixing [ J ]. CHEMICAL MUNICATIONS, 2010, 46(40): 7625-0), but there are no known documents that apply ionic liquids to light hydrocarbon aromatization reactions. Therefore, the invention develops the light hydrocarbon aromatization reaction catalyzed by the ionic liquid for the first time, which has very important significance and use value for the development of aromatization technology. In addition, the method has the advantages of simple preparation process, simple and convenient operation, low cost, good economic benefit and good industrialization potential.
Disclosure of Invention
In order to solve the technical problems, the invention aims to design a method for preparing aromatic hydrocarbon by light hydrocarbon at low temperature. Putting the ionic liquid as a catalyst and a light hydrocarbon raw material into a reaction kettle, and reacting at low temperature in an atmosphere to obtain the aromatic hydrocarbon.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for preparing aromatic hydrocarbon by light hydrocarbon at low temperature specifically comprises the following steps:
(1) synthesis of ionic liquid catalyst: the ionic liquids used in the present invention can be prepared by methods known in the art and known to those skilled in the art.
(2) Light hydrocarbon aromatization process: weighing the ionic liquid catalyst and light hydrocarbon, uniformly mixing the ionic liquid catalyst and the light hydrocarbon in a high-pressure reaction kettle in a mass ratio of 0.01-10, and reacting at low temperature in an atmosphere to obtain the catalystTo aromatic hydrocarbons, wherein the raw material light hydrocarbon is C1-C8An alkane or an alkene of (a).
Further, the ionic liquid is imidazole, pyridine, quaternary ammonium type or quaternary phosphine type ionic liquid, and is a compound represented by the following specific structural formula:
Figure DEST_PATH_IMAGE001
in the formula, X-is AlCl4 -, Al2Cl7 -, CuAlCl5 -, AlBr4 -One or more of; r is C1-C8Any one of the linear alkyl groups of (a); r' is nothing, C1-C8Any one of linear alkyl, -COOH or-SO3H acid radical; n = 1-6.
Further, the reaction pressure is 0-5MPa, the reaction temperature is 0-150 ℃, the catalytic reaction time is 0.5-72 h, and the gas atmosphere is one or two of nitrogen and hydrogen.
The invention has the beneficial effects that:
compared with the existing molecular sieve catalyst, the light hydrocarbon aromatization method provided by the invention can generate aromatic hydrocarbon products at low temperature. Has the following advantages:
(1) the ionic liquid catalyst has the advantages of good solubility, low volatility, high thermal stability, wide liquid existing temperature range, designability, repeatability and the like;
(2) the operation temperature in the experimental process is greatly reduced, the harsh condition of higher reaction temperature in the existing aromatization process of the molecular sieve catalyst is overcome, the energy consumption is reduced, the comprehensive cost of the technology application is reduced, and the method has good economic benefit and industrialization potential.
Detailed Description
The following examples are intended to more fully describe the invention in order to clearly understand the technical features, objects and advantages of the invention, but should not be construed to limit the scope of the invention.
The ionic liquid catalysts used in the following examples were synthesized according to a conventional method.
Example 1
Ionic liquid catalyst A ([ HO ] in a mass ratio of 0.2:1 (based on 10 g of n-hexane)3SC3NEt3]Cl -5AlCl3) Adding n-hexane into an autoclave, introducing nitrogen, controlling the initial pressure to be 0.1 MPa, the stirring speed to be 500 rpm, controlling the reaction temperature to be 20 ℃, and reacting for 3 hours to obtain the total content of aromatic hydrocarbon of 0.888, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
The presumed reaction mechanism of aromatization of n-hexane on ionic liquids is as follows:
Figure DEST_PATH_IMAGE002
firstly, n-hexane forms a carbonium ion intermediate on an L acid position, then an olefin intermediate and a dimer intermediate on a B acid until the intermediates are cyclized, and finally, dehydrogenation is carried out on the L acid position to generate the aromatic hydrocarbon.
Example 2
Ionic liquid catalyst B ([ HO ] 10 g based on n-hexane) in a mass ratio of 1:13SC3NEt3]Cl -5AlCl3) Adding the obtained product and n-hexane into an autoclave, introducing nitrogen, controlling the initial pressure to be 0.5 MPa, the stirring speed to be 500 rpm, controlling the reaction temperature to be 30 ℃, and reacting for 3 hours to obtain the total content of aromatic hydrocarbon of 1.256, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Example 3
Ionic liquid catalyst C ([ HO ] 10 g of n-hexane) in a mass ratio of 1:23SC3NEt3]Cl -5AlCl3-0.67CuCl) and n-hexane were added to the autoclave, nitrogen was introduced, the initial pressure was controlled to 1 MPa, the stirring speed was 500 rpm, the reaction temperature was controlled at 40 ℃, the reaction was carried out for 3 hours, the total content of aromatic hydrocarbons was 1.619, the aromatic hydrocarbons obtained included benzene, toluene and xylene, the specific data are shown in table 1.
Example 4
By the natureIonic liquid catalyst D (BmimCl-3 AlCl) with the weight ratio of 1:1 (based on 10 g of n-hexane)3) Adding the obtained product and n-hexane into an autoclave, introducing nitrogen, controlling the initial pressure to be 1 MPa, the stirring speed to be 500 rpm, controlling the reaction temperature to be 50 ℃, and reacting for 8 hours to obtain the total content of aromatic hydrocarbon of 1.335, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Example 5
Ionic liquid catalyst E (TBAB-3 AlCl) with mass ratio of 1:5 (based on 10 g of n-pentane)3) Adding into autoclave together with n-pentane, introducing nitrogen, controlling initial pressure at 1 MPa, stirring speed at 500 rpm, controlling reaction temperature at 60 deg.C, reacting for 3 h to obtain total content of aromatic hydrocarbon of 0.962, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Example 6
Ionic liquid catalyst F ([ HO ] 10 g based on n-pentane in a mass ratio of 1:13SC3NEt3]Cl -5AlCl3-0.67H2SO4) Adding into a high-pressure autoclave together with n-pentane, introducing nitrogen, controlling the initial pressure to be 1 MPa, the stirring speed to be 500 rpm, controlling the reaction temperature to be 80 ℃, and reacting for 3 h to obtain the total content of aromatic hydrocarbon of 1.610, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Example 7
Ionic liquid catalyst G ([ HO ] 10G based on n-pentene) in a mass ratio of 1:13SC3NEt3]Cl -5AlCl3) Adding the mixture and n-pentene into an autoclave, introducing nitrogen, then releasing gas and closing a valve, controlling the initial pressure to be room pressure, the stirring speed to be 500 rpm, controlling the reaction temperature to be 100 ℃, reacting for 3 hours to obtain the total content of aromatic hydrocarbon of 3.990, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Example 8
Adding an ionic liquid catalyst H ([ HO3SC3NEt3] Cl-5 AlCl3) and n-heptane in a mass ratio of 1:1 (based on 10 g of n-heptane) into an autoclave, introducing nitrogen, then closing a valve by releasing air, controlling the initial pressure to be room pressure, stirring at 500 rpm, controlling the reaction temperature to be 50 ℃, and reacting for 3 hours to obtain the total content of aromatic hydrocarbon of 1.868, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Comparative example 1
This comparative example uses an unmodified ZSM-5 molecular sieve as catalyst for comparison with example 1.
ZSM-5 molecular sieve catalyst and n-hexane in a mass ratio of 1:3 (based on 10 g of n-hexane) are added into an autoclave, nitrogen is introduced, the initial pressure is controlled to be 1 MPa, the stirring speed is 500 rpm, the reaction temperature is controlled to be 20 ℃, and the reaction is carried out for 3 hours.
Comparative example 2
This comparative example uses an unmodified ZSM-5 molecular sieve as catalyst for comparison with example 1.
ZSM-5 molecular sieve catalyst and n-hexane in a mass ratio of 1:3 (based on 10 g of n-hexane) are added into an autoclave, nitrogen is introduced, the initial pressure is controlled to be 1 MPa, the stirring speed is 500 rpm, the reaction temperature is controlled to be 50 ℃, and the reaction is carried out for 3 hours.
Comparative example 3
This comparative example uses an unmodified ZSM-5 molecular sieve as catalyst for comparison with example 1.
ZSM-5 molecular sieve catalyst and n-heptane with the mass ratio of 1:3 (based on 10 g of n-heptane) are added into an autoclave, nitrogen is introduced, the initial pressure is controlled to be 1 MPa, the stirring speed is 500 rpm, the reaction temperature is controlled to be 50 ℃, and the reaction lasts for 3 hours.
Comparative example 4
This comparative example uses an unmodified ZSM-5 molecular sieve as catalyst for comparison with example 1.
ZSM-5 molecular sieve catalyst and n-hexane in a mass ratio of 1:3 (based on 10 g of n-hexane) are added into an autoclave, nitrogen is introduced, the initial pressure is controlled to be 1 MPa, the stirring speed is 500 rpm, the reaction temperature is controlled to be 100 ℃, and the reaction is carried out for 24 hours.
Figure 968605DEST_PATH_IMAGE003
As can be seen from the data in table 1, the ionic liquid catalyst of the present invention has significant aromatization activity, and thus has the capability of light hydrocarbon aromatization. Compared with the comparative example, the traditional molecular sieve catalyst has the catalytic activity of light hydrocarbon aromatization at low temperature. Therefore, the ionic liquid catalyst has the capability of catalyzing light hydrocarbons to be converted into aromatic hydrocarbons at low temperature, is simple and convenient to operate, has low cost, and has good economic benefits and industrial potential.
It should be understood that the above examples are illustrative for clarity and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. Nor is it intended to be exhaustive of all embodiments. Rather, obvious variations or modifications are possible without departing from the scope of the invention.

Claims (7)

1. A method for preparing aromatic hydrocarbon from light hydrocarbon at low temperature is characterized by comprising the following steps: the ionic liquid is used as a catalyst, and the ionic liquid and the light hydrocarbon raw material are placed in a reaction kettle to be uniformly mixed and reacted to obtain the aromatic hydrocarbon under the gas atmosphere.
2. The method for preparing the aromatic hydrocarbon by the light hydrocarbon at low temperature according to claim 1, which is characterized in that: the ionic liquid is imidazole, pyridine, quaternary ammonium type or quaternary phosphine type ionic liquid, and is a compound represented by the following specific structural formula:
Figure 609463DEST_PATH_IMAGE001
in the formula, X-is AlCl4 -, Al2Cl7 -, CuAlCl5 -, AlBr4 -One or more of; r is C1-C8Any one of the linear alkyl groups of (a); r' is nothing, C1-C8Any one of linear alkyl, -COOH or-SO3H acid radical; n = 1-6.
3. The method of claim 1, wherein: the light hydrocarbon raw material is C1-C8An alkane or an alkene of (a).
4. The method of claim 1, wherein: the mass ratio of the ionic liquid to the light hydrocarbon raw material is 0.01-10.
5. The method of claim 1, wherein: the reaction temperature is 0-150 ℃, and the reaction pressure is 0-5 MPa.
6. The method of claim 1, wherein: the gas atmosphere is one or two of nitrogen and hydrogen.
7. The method of claim 1, wherein: the reaction time is 0.5-72 h.
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US20030060359A1 (en) * 2001-08-31 2003-03-27 Institut Francais Du Petrole Composition of catalyst and solvent and catalysis processes using this composition
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US20150210609A1 (en) * 2014-01-30 2015-07-30 Uop Llc Ionic liquid alkylation of 1-butene to produce 2,5-dimethylhexane
CN106964401A (en) * 2017-04-06 2017-07-21 福州大学 A kind of light paraffins isomerization ionic-liquid catalyst and preparation method thereof
WO2017200625A1 (en) * 2016-05-19 2017-11-23 Chevron U.S.A. Inc. High viscosity index lubricants by isoalkane alkylation
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US20030060359A1 (en) * 2001-08-31 2003-03-27 Institut Francais Du Petrole Composition of catalyst and solvent and catalysis processes using this composition
CN104447176A (en) * 2013-09-13 2015-03-25 苏州奥索特新材料有限公司 Method for high-selectivity preparation of p-xylene
US20150210609A1 (en) * 2014-01-30 2015-07-30 Uop Llc Ionic liquid alkylation of 1-butene to produce 2,5-dimethylhexane
WO2017200625A1 (en) * 2016-05-19 2017-11-23 Chevron U.S.A. Inc. High viscosity index lubricants by isoalkane alkylation
CN106964401A (en) * 2017-04-06 2017-07-21 福州大学 A kind of light paraffins isomerization ionic-liquid catalyst and preparation method thereof
CN109280561A (en) * 2018-11-29 2019-01-29 北京惠尔三吉绿色化学科技有限公司 A kind of method of naphtha or the low-temperature catalyzed reaction propylene co-production aromatic hydrocarbons processed of lighter hydrocarbons

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Application publication date: 20200417