CN111423303A - Low-temperature aromatization method - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0279—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the cationic portion being acyclic or nitrogen being a substituent on a ring
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
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Abstract
The invention belongs to the technical field of petrochemical industry, and particularly relates to a low-temperature aromatization method. The invention uses Bronsted acid-Lewis acid double-acid ionic liquid as a catalyst, and uses cyclane containing tertiary carbon atoms as a product distribution regulator. Carrying 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 uses the cycloparaffin containing tertiary carbon atoms as an aromatization product regulator 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
Technical Field
The invention belongs to the field of petrochemical industry, and particularly relates to a low-temperature aromatization method.
Background
Aromatic hydrocarbons generally refer to Benzene (Benzene, abbreviated as B), Toluene (Toluene, abbreviated as T), and Xylene (Xylene, abbreviated as X) are important basic chemical raw materials, and are also common blending components for adjusting octane number of gasoline. In recent years, the demand of aromatic hydrocarbon in China is rapidly increased, and the development of productivity and yield is seriously delayed, so that the improvement of the productivity and yield of aromatic hydrocarbon and the research and development of a new aromatic hydrocarbon technology are not easy. 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 of the technology is the research and development of a catalyst and the development of a catalytic process.
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, and the reaction temperature is relatively high. Such as Pt/Al supported Pt/Al developed by British oil company (BP) and U.S. UOP2O3、Pd/Al2O3Catalyst, at a reaction temperature higher than 550 ℃, for the conversion of alkanes into aromatic hydrocarbons, the reaction being accompanied byAlong with severe cracking side reaction, Pt and Pd are noble metals, and the cost is high (Csic series S. dehydration of vapors overlappered playtime [ J ]]Journal of Catalysis, 1970, 17: 207-. HZSM-5 as a catalyst of Mobile company in the United states reduces the aromatization reaction temperature to 425 ℃, but serious carbon deposition still occurs in the reaction process (Chen N, Yan Y. M2-formation-A process for the formation of light hydrocarbons [ J]. Industrial&Engineering Chemistry Design and Development, 1986,25: 151- & 155, preparation and reaction Studies 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 a catalyst, the aromatization selectivity is improved, and simultaneously the reaction temperature is as high as 500 ℃, the industrial catalysts are mostly required to be operated under higher temperature and hydrogen atmosphere, and the defects of active component loss, carbon deposition and high energy consumption and cost are easy to occur.
The ionic liquid catalyst with Lewis acid acidity is generally used in alkane alkylation reaction (Cui, P, ZHAO G, Ren H, et al. Ionic liquid enhanced alkylation of iso-butyl and 1-butyl [ J ]. Catalysis Today,2013, 200: 30-35) and Isomerization reaction (Zhang R, Meng X, L iu Z, et al. isometry of n-branched carboxylic acid catalyzed by ionic liquid [ J ]. Industral & Engineering chemical Research, 2008, 47: 8205) the invention firstly develops a Bronsted acid-Lewis acid ionic liquid as a catalyst, and the invention has great economic benefits for the preparation of tertiary carbon atoms, simple operation technology and low cost for cycloparaffinization process.
Disclosure of Invention
In order to solve the technical problems, the invention aims to design a low-temperature aromatization method. The Bronsted acid-Lewis acid diacid ionic liquid is used as a catalyst, cycloalkane containing tertiary carbon atoms is used as a product distribution regulator, and the product distribution regulator and a light hydrocarbon raw material are placed in a reaction kettle and react 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 low-temperature aromatization method specifically comprises the following steps:
(1) synthesizing a Bronsted acid-Lewis acid double-acid 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) Low-temperature aromatization process: weighing the ionic liquid catalyst, the cyclane containing the tertiary carbon atom and the light hydrocarbon, and uniformly mixing in a high-pressure reaction kettle, wherein the mass ratio of the ionic liquid catalyst to the light hydrocarbon is 0.01-10, and the mass ratio of the light hydrocarbon to the cyclane containing the tertiary carbon atom is 0.01-0.1. And reacting at low temperature in an atmosphere to obtain the aromatic hydrocarbon.
Wherein the raw material light hydrocarbon is C1-C8The alkane or alkene and tertiary carbon atom cyclic alkane product distribution regulator is any one of monocyclic or bicycloalkane of methylcyclohexane, methylcyclopentane, (o-, m-, p-) dimethylcyclohexane and 2, 2, 6-trimethylcycloheptane.
Wherein, the Bronsted acid-Lewis acid double-acid ionic liquid is any one of imidazole, pyridine, quaternary ammonium type or quaternary phosphine type ionic liquid, and is a compound represented by the following specific structural formula:
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, -PO4H2or-SO3H acid radical; n = 1-6.
Further, the reaction pressure is 0-1 MPa, the reaction temperature is 0-120 ℃, the catalytic reaction time is 0.5-60 h, and the gas atmosphere is one or two of nitrogen and hydrogen.
The invention has the advantages that:
compared with the existing molecular sieve catalyst, the light hydrocarbon aromatization method provided by the invention synthesizes aromatic hydrocarbon products with high yield by taking tertiary carbon atom cycloparaffin as a product regulator 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 pressure and temperature in the experimental process are greatly reduced, the harsh condition of higher reaction temperature in the existing molecular sieve catalyst aromatization process is overcome, the energy consumption is reduced, the comprehensive cost of the technology application is reduced, the aromatic hydrocarbon yield is obviously improved by adding the distribution regulator of the cycloalkane product containing tertiary carbon atoms, and the method has good economic benefit and industrialization potential.
Drawings
FIG. 1 shows the proposed reaction mechanism for aromatization of n-hexane on ionic liquids.
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) (preparation method is referred to Industrial&Engineering Chemistry Research, 2008, 47:8205-The temperature is controlled at 20 ℃, the reaction is carried out for 3 hours, the total content of the obtained aromatic hydrocarbon is 0.888, the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in table 1.
The reaction mechanism of the aromatization of n-hexane on ionic liquids is assumed as follows in fig. 1:
firstly, n-hexane forms a carbonium ion intermediate on acid position L, then an olefin intermediate and a dimer intermediate on acid B until the intermediate is cyclized, and finally dehydrogenation is carried out on acid position L to generate aromatic hydrocarbon, wherein the addition of the cycloalkane containing tertiary carbon atoms stabilizes the carbonium ion and induces the generation of cycloalkane intermediates, thereby improving the yield of the aromatic hydrocarbon.
Example 2
Ionic liquid catalyst A ([ HO ] in a mass ratio of 0.1:0.02:1 (based on 10 g of n-hexane)3SC3NEt3]Cl -5AlCl3) Adding methylcyclohexane and 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.
Example 3
Ionic liquid catalyst A ([ HO ] in a mass ratio of 0.1:0.05:1 (based on 10 g of n-hexane)3SC3NEt3]Cl -5AlCl3) Adding methylcyclohexane 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 1.256, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Example 4
Ionic liquid catalyst B ([ HO ] in a mass ratio of 0.1:0.1:1 (based on 10 g of n-hexane)3SC3NEt3]Br -5AlBr3) Adding (the compound is a self-made compound), methylcyclopentane 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 h to obtain the total content of aromatic hydrocarbon 1.256, wherein the obtained aromatic hydrocarbon comprises benzene and methylBenzene and xylene, specific data are shown in table 1.
Example 5
Ionic liquid catalyst C ([ HO ] 10 g of n-hexane) in a mass ratio of 1:23SC3NEt3]Cl -5AlCl3-0.67CuCl), adding methylcyclopentane and n-hexane (the mass ratio of the two is 0.01-0.1) 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 40 ℃, and reacting for 3 hours to obtain the total content of aromatic hydrocarbon of 1.619, wherein the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data is shown in Table 1.
Example 6
Ionic liquid catalyst C ([ HO ] in a mass ratio of 0.2:0.1:2 (based on 10 g of n-hexane)3SC3NEt3]Cl -5AlCl3-0.67CuCl), p-dimethylcyclohexane and 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 40 ℃, the reaction is carried out for 3 hours, the total content of the obtained aromatic hydrocarbon is 1.619, the obtained aromatic hydrocarbon comprises benzene, toluene and xylene, and the specific data are shown in Table 1.
Example 7
Ionic liquid catalyst A ([ HO ] in a mass ratio of 1:1 (based on 10 g of n-pentene)3SC3NEt3]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
Ionic liquid catalyst A ([ HO ] in a mass ratio of 0.01:0.1:1 (based on 10 g of n-pentene)3SC3NEt3]Cl -5AlCl3) Adding methylcyclohexane and n-pentene into an autoclave, introducing nitrogen, then releasing gas and closing a valve, controlling the initial pressure to be room pressure, 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 6.698, 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-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.
Table 1 table for light hydrocarbon aromatization results
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 (9)
1. A low temperature aromatization process characterized by: the method comprises the steps of taking Bronsted acid-Lewis acid diacid ionic liquid as a catalyst, taking cycloalkane containing a tertiary carbon atom as a product distribution regulator, placing the ionic liquid, the cycloalkane containing the tertiary carbon atom and a light hydrocarbon raw material in a reaction kettle in a gas atmosphere, uniformly mixing and reacting to obtain the aromatic hydrocarbon.
2. The low temperature aromatization process of claim 1 wherein: the Bronsted acid-Lewis acid diacid ionic liquid is any one of imidazole, pyridine, quaternary ammonium type or quaternary phosphine type diacid ionic liquid, and is a compound represented by the following specific structural formula:
in the formula, X-is AlCl4 -, Al2Cl6Br-, GaCl4 -, 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 and-PO4H2or-SO3H acid radical; n = 1-6.
3. The low temperature aromatization process of claim 1 wherein: the tertiary carbon atom-containing cycloparaffin product distribution regulator is any one of monocyclic or bicycloalkane of methylcyclohexane, methylcyclopentane, (o-, m-, p-) dimethylcyclohexane and 2, 2, 6-trimethylcycloheptane.
4. The low temperature aromatization process of claim 1 wherein: the light hydrocarbon raw material is C1-C8An alkane or an alkene of (a).
5. The low temperature aromatization process of claim 1 wherein: the mass ratio of the tertiary carbon atom naphthenic product distribution regulator to the light hydrocarbon raw material is 0.01-0.1.
6. The low temperature aromatization process of claim 1 wherein: the mass ratio of the ionic liquid to the light hydrocarbon raw material is 0.01-10.
7. The low temperature aromatization process of claim 1 wherein: the reaction temperature is 0-120 ℃, and the reaction pressure is 0-1 MPa.
8. The low temperature aromatization process of claim 1 wherein: the gas atmosphere is one or two of nitrogen and hydrogen.
9. The low temperature aromatization process of claim 1 wherein: the reaction time is 0.5-60 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 |
| 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 |
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