CN106582792B - The catalyst of benzene and ethane alkylated reaction - Google Patents
The catalyst of benzene and ethane alkylated reaction Download PDFInfo
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Abstract
The present invention relates to the catalyst of benzene and ethane alkylated reaction, mainly solve the problems, such as that alkylation of the molecular sieve carried Pt catalyst between benzene and ethane answers the conversion ratio of middle benzene and ethane low, catalyst of the present invention by using benzene and ethane alkylated reaction, including following components: (a) Pt or its oxide；(b) oxide of Sn；(c) simple substance or oxide of La series elements；(d) technical solution of molecular sieve preferably solves the technical problem, can be used in the alkylated reaction that benzene and ethane carry out.
Description
Technical field
The present invention relates to the catalyst of benzene and ethane alkylated reaction.
Background technique
Shale gas is a kind of important unconventional gas resource of rising in recent years." the shale gas revolution " in the U.S. has been moved
Global Natural Gas Market pattern pattern is shaken, and this influence will also be more significant, and then change world energy sources general layout.Shale
The development and utilization of gas, it has also become the important impetus and world's oil-gas geopolitics configuration structure of low-carbon economy strategic development opportunity
Property adjustment catalyst.China's shale gas is resourceful, and a large amount of ethane of shale gas association, natural gas, casing-head gas and refinery
It is cheap also containing low-carbon alkanes such as a large amount of ethane in gas.But since ethane structure is highly stable, it is difficult to activate, be difficult conduct
The raw material of industry is directly applied.Currently, ethane is mainly used to pass through producing ethylene by cracking in chemical industry.Ethane is mixed with steam
Conjunction is cracked in 900 DEG C or more of high temperature, is consumed energy high.Efficient Conversion is always to urge using ethane in a mild condition
Change the hot spot of area research.In recent years, foreign literature proposes a kind of new method utilized for low-carbon alkanes such as ethane, by second
Alkane is alkylated with benzene to react, can synthesizing ethyl benzene at a lower temperature, the alkylbenzenes such as diethyl benzene,toluene,xylene.Its
In, ethylbenzene is that the important commercialization derivative of benzene in current chemical industry is also used to organic synthesis mainly for the production of styrene
Intermediate pharmaceutically can also make solvent use.Ethylbenzene yield occupies sizable specific gravity in basic organic chemical industry,
Annual consumption is huge.Styrene is the important foundation raw material of petrochemical industry, mainly for the production of styrene series resin and butylbenzene
Rubber, and production one of ion exchange resin and the raw material of pharmaceuticals, in addition, styrene can also be used in pharmacy, dyestuff, pesticide
And the industries such as ore dressing.The homopolymer polystyrene of styrene is one of five big general thermoplastic synthetic resins, is widely used in note
Mould product, extruded product and the big field of foamed product 3.And ethylbenzene be produce styrene critical materials, industrial 90% or more
Styrene be made by ethylbenzene.Therefore, using the alkylbenzenes such as ethane and one step alkylated reaction synthesizing ethyl benzene of benzene, may be implemented with
Shale gas etc. is the direct conversion of the large petrochemicals of material downstream, has great research significance and application value.
Currently, external, only quantifier elimination reports reacting for the alkylbenzenes such as ethane and benzene direct alkylation ethylbenzene less.
Document Journal of the American Chemical Society, 1975,97:6807-6810 report superpower earliest
Acid catalyst HF-SbF5The alkylated reaction of upper ethane and benzene, ethylbenzene selectivity 76%, but yield only 1%.Document
Catalysis Letters, 2001,73:175-180 report second on the ZSM-5 molecular sieve catalyst of the Pt load of 6.8wt%
The alkylated reaction of alkane and benzene, ethylbenzene yield is up to 7.3% at 500 DEG C, and the conversion ratio of benzene is 8.3% at this time, and in addition there are second
Alkene and a small amount of styrene generate, and document does not provide the selectivity of each product.Document Journal of Molecular
Catalysis A:Chemical, 2008,279:128-132 is reported on the ZSM-5 molecular sieve catalyst of 1wt%Pt load,
Benzene alkane molar ratio is 1/9, mass space velocity 3.1h-1When, ethane conversion is lower than 2%, in the alkylbenzene product of generation, ethylbenzene
Selectivity is 92.6%, and the selectivity of toluene is 0.99%, and the selectivity of diethylbenzene is 2.3%.
In the document of above disclosure report, Pt/ZSM-5 molecular sieve catalyst is all made of to be supported on for single Pt element
On ZSM-5 molecular sieve, the conversion ratio of ethane and benzene is lower, and precious metals pt dosage is larger.
Summary of the invention
The first technical problem to be solved by the present invention is molecular sieve carried Pt catalyst for the alkane between benzene and ethane
The problem that base answers the conversion ratio of middle benzene and ethane low provides the new benzene of one kind and is alkylated the catalyst reacted with ethane,
The catalyst has the advantages that the high conversion rate of benzene and ethane.
The second technical problem to be solved by the present invention is to provide the preparation of catalyst described in one of above-mentioned technical problem
Method.
The third technical problem to be solved by the present invention is to provide the benzene using catalyst described in one of above-mentioned technical problem
Alkylation reaction method between ethane.
One of to solve above-mentioned technical problem, technical scheme is as follows: the catalysis of benzene and ethane alkylated reaction
Agent, including following components:
(a) Pt or its oxide；
(b) oxide of Sn；
(c) simple substance or oxide of La series elements；
(d) molecular sieve.
In above-mentioned technical proposal, Pt and Sn have synergistic effect.
In above-mentioned technical proposal, based on parts by weight, composition (a) is preferably 0.1~5 part, and more preferable 0.3~2 part.
In above-mentioned technical proposal, based on parts by weight, composition (b) is preferably 0.1~5 part, and more preferable 0.3~2 part.
In above-mentioned technical proposal, based on parts by weight, composition (c) is preferably 0.1~5 part.
In above-mentioned technical proposal, based on parts by weight, composition (d) is preferably 80~100 parts.
In above-mentioned technical proposal, the La series elements preferably are selected from least one of La, Ce, Pr and Nd；The La system member
Plain more preferably include Ce and Pr simultaneously, has synergistic effect between two kinds of La series elements.
In above-mentioned technical proposal, the molecular sieve is hydrogen type molecular sieve.
In above-mentioned technical proposal, the molecular sieve be ZSM-5, Beta molecular sieve, MCM-22, in ZSM-35 molecular sieve extremely
Few one kind.The Si/Al molar ratio of molecular sieve is not particularly limited, and those skilled in the art can reasonably select.Such as it is but unlimited
In when using ZSM-5 molecular sieve, optional Si/Al molar ratio is 20~300.
In above-mentioned technical proposal, more preferably in parts by weight, composition includes: the composition of the catalyst
(a) 0.1~5 part of Pt or its oxide；
(b) oxide of 0.1~5 part of Sn；
(c) simple substance or oxide of 0.1~5 part of La series elements；
(d) 80~100 parts of molecular sieves.
To solve above-mentioned technical problem two, technical scheme is as follows: stating the technical solution of one of technical problem
Described in catalyst preparation method, include the following steps:
(1) it disperses the compound of the compound containing Pt, the compound containing Sn and the series elements containing La in solvent；
(2) dispersion for obtaining step (1) impregnates the molecular sieve；
(3) it roasts.
In above-mentioned technical proposal, the compound containing Pt and the compound containing Sn are not particularly limited, this field skill
Art personnel can reasonably select, the such as, but not limited to described compound containing Pt be chloroplatinic acid, Sn compound can be but not
It is limited to stannous chloride, nitric acid tin, carboxylic acid stannous.The compound of the series elements containing La, such as, but not limited to nitrate, chloride
Deng.
The solvent that step (1) uses is not particularly limited, as long as being able to achieve the operation of dip loading, these solvents can
To be to dissolve, or by adjusting pH dissolution, be also possible to that colloid or molten by adjusting those of pH formation colloid can be formed
Agent can be single solvent, or mixed solvent.
In above-mentioned technical proposal, one skilled in the art will appreciate that drying can be inserted between step (2) and step (3)
The step of to improve the intensity of catalyst.Dry condition is not particularly limited, such as dry optional 60~120 DEG C of temperature,
The dry time optional 2~for 24 hours.
In above-mentioned technical proposal, the temperature of roasting is preferably 400~600 DEG C.
In above-mentioned technical proposal, the time of roasting is preferably 1~12h, more preferable 1~5h.
In above-mentioned technical proposal, Pt can exist in the form of an oxide in the commercial form of the catalyst, Sn element with
SnO2Form exist, but using preceding needing to be reduced to Pt metal with the oxide of reducing agent Pt, by SnO2It is restored to the shape of SnO
Formula；Or Pt element can exist in the form of Pt metal in the commercial form of the catalyst, Sn element is deposited in the form of SnO
Only including the steps that reduction after firing in the preparation process of catalyst at this time.Those skilled in the art know
Road rationally determines actual reducing condition, such as, but not limited to: being reduction with pure hydrogen or hydrogen and inert gas mixture
Agent (such as, but not limited to hydrogen-nitrogen gaseous mixture, hydrogen-helium mix gas etc.).
To solve above-mentioned technical problem three, technical scheme is as follows: benzene, which is alkylated with ethane, to react
Method, in the presence of the catalyst described in any one of technical solution of one of above-mentioned technical problem, using benzene and ethane as raw material into
Row reaction obtains alkylates.
In above-mentioned technical proposal, reaction temperature is preferably 300~600 DEG C.
In above-mentioned technical proposal, reaction pressure is preferably 0~0.5MPa.
In above-mentioned technical proposal, material quality air speed is preferably 1~15h-1。
In above-mentioned technical proposal, the molar ratio of ethane and benzene is preferably (1~20) in raw material: 1.
The present invention introduces La series elements in Pt-Sn/ZSM-5 catalyst, improves the conversion ratio of ethane and benzene.For example,
When catalyst includes Ce and Pr simultaneously, have between two kinds of La series elements and act synergistically, on Pt-Zn-Ce-Pr/ZSM-5 catalyst
Up to 7.1%, benzene high conversion rate can be used in the glycosylation reaction of benzene and ethane the high conversion rate of ethane up to 24.8%.
The present invention will be further described below by way of examples, but these embodiments are not to the scope of the present invention
It is limited.
Specific embodiment
[embodiment 1]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O) and it is equivalent to 0.35g CeO2Cerous nitrate
(molecular formula is Ce (NO3)3·6H2O it) is added in 50mL deionized water, stirring dissolves it all, is formed material (I)；It weighs
It is equivalent to stannous chloride (the molecular formula SnCl of 0.65g SnO2·2H2O it) is added in 50mL dehydrated alcohol, stirring keeps it complete
Portion's dissolution, forms material (II)；Material (II) is added in material (I), 1h is stirred, is formed material (III)；Weigh 98.5g's
Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46), is then added in material (III), impregnates 4h, 100 DEG C of dry 12h,
500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
Benzene carries out on continuous fixed bed reactor with ethane alkylated reaction, and Catalyst packing quality is 2.7g.
Before reaction, then temperature of reactor is adjusted to reaction temperature, feed ethan is passed through and is reacted with benzene.Reaction condition are as follows: anti-
480 DEG C of temperature, reaction pressure 0.1MPa are answered, the mass space velocity of raw material is 6.5h-1, the molar ratio of ethane and benzene is 7.Reaction knot
Fruit is shown in Table 2.
[embodiment 2]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O) and it is equivalent to 0.35g Pr2O3Praseodymium nitrate
(molecular formula is Pr (NO3)3·6H2O it) is added in 50mL deionized water, stirring dissolves it all, is formed material (I)；It weighs
It is equivalent to stannous chloride (the molecular formula SnCl of 0.65g SnO2·2H2O it) is added in 50mL dehydrated alcohol, stirring keeps it complete
Portion's dissolution, forms material (II)；Material (II) is added in material (I), 1h is stirred, is formed material (III)；Weigh 98.5g's
Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46), is then added in material (III), impregnates 4h, 100 DEG C of dry 12h,
500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
The catalyst ethane and benzene alkylation reaction performance are evaluated according to the same manner as in Example 1.Reaction result is shown in Table
2。
[embodiment 3]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O), it is equivalent to 0.23g CeO2Cerous nitrate
(molecular formula is Ce (NO3)3·6H2O) and it is equivalent to 0.12g Pr2O3Praseodymium nitrate (molecular formula be Pr (NO3)3·6H2O it) is added
Into 50mL deionized water, stirring dissolves it all, is formed material (I)；Weigh the stannous chloride for being equivalent to 0.65g SnO
(molecular formula SnCl2·2H2O it) is added in 50mL dehydrated alcohol, stirring dissolves it all, is formed material (II)；By material
(II) it is added in material (I), stirs 1h, formed material (III)；Weigh Hydrogen ZSM-5 molecular sieve (the Si/Al molar ratio of 98.5g
46), to be then added in material (III), 4h, 100 DEG C of dry 12h, 500 DEG C of roasting 2h are impregnated.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
The catalyst ethane and benzene alkylation reaction performance are evaluated according to the same manner as in Example 1.Reaction result is shown in Table
2。
[embodiment 4]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O), it is equivalent to 0.23g CeO2Cerous nitrate
(molecular formula is Ce (NO3)3·6H2O) and it is equivalent to 0.12g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into 50mL deionized water, stirring dissolves it all, is formed material (I)；Weigh the stannous chloride for being equivalent to 0.65g SnO
(molecular formula SnCl2·2H2O it) is added in 50mL dehydrated alcohol, stirring dissolves it all, is formed material (II)；By material
(II) it is added in material (I), stirs 1h, formed material (III)；Weigh Hydrogen ZSM-5 molecular sieve (the Si/Al molar ratio of 98.5g
46), to be then added in material (III), 4h, 100 DEG C of dry 12h, 500 DEG C of roasting 2h are impregnated.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
The catalyst ethane and benzene alkylation reaction performance are evaluated according to the same manner as in Example 1.Reaction result is shown in Table
2。
[embodiment 5]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O), it is equivalent to 0.1g CeO2Cerous nitrate
(molecular formula is Ce (NO3)3·6H2O) and it is equivalent to 0.25g Pr2O3Praseodymium nitrate (molecular formula be Pr (NO3)3·6H2O it) is added
Into 50mL deionized water, stirring dissolves it all, is formed material (I)；Weigh the stannous chloride for being equivalent to 0.65g SnO
(molecular formula SnCl2·2H2O it) is added in 50mL dehydrated alcohol, stirring dissolves it all, is formed material (II)；By material
(II) it is added in material (I), stirs 1h, formed material (III)；Weigh Hydrogen ZSM-5 molecular sieve (the Si/Al molar ratio of 98.5g
46), to be then added in material (III), 4h, 100 DEG C of dry 12h, 500 DEG C of roasting 2h are impregnated.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
The catalyst ethane and benzene alkylation reaction performance are evaluated according to the same manner as in Example 1.Reaction result is shown in Table
2。
[comparative example 1]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O) and it is equivalent to 0.35g CeO2Cerous nitrate
(molecular formula is Ce (NO3)3·6H2O it) is added in 50mL deionized water, stirring dissolves it all, is formed material (I)；It weighs
The Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46) of 98.5g, is then added in material (I), impregnates 4h, 100 DEG C of dryings
12h, 500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
The catalyst ethane and benzene alkylation reaction performance are evaluated according to the same manner as in Example 1.Reaction result is shown in Table
2。
[comparative example 2]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O) and it is equivalent to 0.35g Pr2O3Praseodymium nitrate
(molecular formula is Pr (NO3)3·6H2O it) is added in 50mL deionized water, stirring dissolves it all, is formed material (I)；It weighs
The Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46) of 98.5g, is then added in material (I), impregnates 4h, 100 DEG C of dryings
12h, 500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
The catalyst ethane and benzene alkylation reaction performance are evaluated according to the same manner as in Example 1.Reaction result is shown in Table
2。
[comparative example 3]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 0.5g2PtCl6·6H2O it) is added in 50mL deionized water, stirs
It dissolves it all, is formed material (I)；Weigh stannous chloride (the molecular formula SnCl for being equivalent to 0.65g SnO2·2H2O) add
Enter into 50mL dehydrated alcohol, stirring dissolves it all, is formed material (II)；Material (II) is added in material (I), stirring
1h is formed material (III)；The Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46) for weighing 98.5g, is then added to material
(III) in, 4h, 100 DEG C of dry 12h, 500 DEG C of roasting 2h are impregnated.
Above-mentioned product tabletting is crushed to 20~40 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 350 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
The catalyst ethane and benzene alkylation reaction performance are evaluated according to the same manner as in Example 1.Reaction result is shown in Table
2。
By embodiment with comparative example it is found that La series elements are shown with Pt and Sn element in terms of improving ethane conversion
Facilitation is cooperateed with, and also shows collaboration facilitation between two kinds of La series elements of Ce and Pr.
1 catalyst of table forms (indicating with weight percentage)
| Pt | SnO | CeO2 | Pr2O3 | La2O3 | ZSM-5 | |
| Embodiment 1 | 0.5 | 0.65 | 0.35 | - | - | 98.5 |
| Embodiment 2 | 0.5 | 0.65 | - | 0.35 | - | 98.5 |
| Embodiment 3 | 0.5 | 0.65 | 0.23 | 0.12 | - | 98.5 |
| Embodiment 4 | 0.5 | 0.65 | 0.23 | - | 0.12 | 98.5 |
| Embodiment 5 | 0.5 | 0.65 | 0.1 | 0.25 | - | 98.5 |
| Comparative example 1 | 0.5 | - | 0.35 | - | - | 99.15 |
| Comparative example 2 | 0.5 | - | - | 0.35 | - | 99.15 |
| Comparative example 3 | 0.5 | 0.65 | - | - | - | 98.85 |
2 evaluating catalyst result of table
Claims (3)
1. the catalyst of benzene and ethane alkylated reaction, including following components:
(a) Pt or its oxide；
(b) oxide of Sn；
(c) simple substance or oxide of La series elements；
(d) molecular sieve, wherein
Based on parts by weight, composition (a) is 0.1~0.5 part, and composition (b) is 0.1~0.65 part, and composition (c) is 0.1~0.35
Part, composition (d) is 80~100 parts；The La series elements are Ce and Pr；The molecular sieve is ZSM-5, Beta molecular sieve, MCM-
22, at least one of ZSM-35 molecular sieve.
2. the preparation method of catalyst described in claim 1, includes the following steps:
(1) it disperses the compound containing Pt, the compound containing Sn and the compound containing the La series elements in solvent；
(2) dispersion for obtaining step (1) impregnates the molecular sieve；
(3) it roasts.
3. the synthetic method of ethylbenzene, using ethane and benzene as raw material, reaction obtains second in the presence of the catalyst described in claim 1
Benzene.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101045207A (en) * | 2006-03-27 | 2007-10-03 | 中国石油化工股份有限公司 | Alkyltransfering catalyst for increasing yield C8 aromatic hydrocarbons |
| CN103121914A (en) * | 2011-11-18 | 2013-05-29 | 中国石油化工股份有限公司 | Toluene disproportionation and transalkylation catalyst and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101045207A (en) * | 2006-03-27 | 2007-10-03 | 中国石油化工股份有限公司 | Alkyltransfering catalyst for increasing yield C8 aromatic hydrocarbons |
| CN103121914A (en) * | 2011-11-18 | 2013-05-29 | 中国石油化工股份有限公司 | Toluene disproportionation and transalkylation catalyst and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| Temperature effects in benzene alkylation with ethane into ethylbenzene over a PtH-MFI bifunctional catalyst;Kae S. Wong et al;《Applied Catalysis A: General》;20130126;第454卷;第137-144页 |
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