CN106582796B - The catalyst of ethane and benzene alkylation reaction - Google Patents
The catalyst of ethane and benzene alkylation reaction Download PDFInfo
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Abstract
The present invention relates to the catalyst of ethane and benzene alkylation reaction, mainly solve the problems, such as that molecular sieve carried Pt catalyst is low with the conversion ratio of ethane in benzene alkylation reaction for ethane, catalyst of the present invention by using ethane and benzene alkylation reaction, including following components: (a) Pt or its oxide；(b) oxide of Zn；(c) at least one of metal oxide in VIB or IIIA；(d) technical solution of molecular sieve preferably solves the technical problem, can be used in the glycosylation reaction of ethane and benzene.
Description
Technical field
The present invention relates to the catalyst of ethane and benzene alkylation reaction.
Background technique
Shale gas is a kind of important unconventional gas resource of rising in recent years, the especially " shale gas since the U.S.
After revolution ", shale gas develops and uses the pattern for significantly affecting and changing world energy sources chemical industry.China's shale gas resource is rich
Richness, and a large amount of ethane of shale gas association, also containing the low-carbon alkanes such as a large amount of ethane, price in natural gas, casing-head gas and refinery gas
Cheaply.But ethane structure is highly stable, it is difficult to activate, be difficult directly to apply as the raw material of industry.Currently, main in chemical industry
To be used to convert ethane to ethylene by steam cracking, to carry out, consume energy high at a high temperature of 900 DEG C or more.In temperature
It is always the hot spot of catalytic field research that Efficient Conversion, which utilizes ethane, under the conditions of.In recent years, foreign literature proposes a kind of use
In the new method that the low-carbon alkanes such as ethane utilize, ethane and benzene are alkylated reaction, can be synthesized at a lower temperature
Ethylbenzene, the alkylbenzenes such as diethyl benzene,toluene,xylene.Wherein, ethylbenzene is that the important commercialization of benzene in current chemical industry is derivative
Object is also used to organic synthesis and intermediate pharmaceutically, can also make solvent use mainly for the production of styrene.Ethylbenzene yield
Occupy sizable specific gravity in basic organic chemical industry, annual consumption is huge.Styrene is the important foundation of petrochemical industry
Raw material is also used to the industries such as pharmacy, dyestuff, pesticide and ore dressing mainly for the production of styrene series resin and butadiene-styrene rubber.
The homopolymer polystyrene of styrene is one of five big general thermoplastic synthetic resins, is widely used in injection-molded item, extruded product
And the fields such as foamed product.And ethylbenzene is the critical materials for producing styrene, the styrene of the industrial overwhelming majority is by ethylbenzene system
?.Therefore, using alkylbenzenes such as one step alkylated reaction synthesizing ethyl benzenes of ethane and benzene, shale gas may be implemented and be converted into down
Large petrochemicals are swum, there is very important research significance and application value.
Currently, the external research for there was only the alkylbenzenes such as the ethane and producing phenylethane from alkylation of benzene reaction of a small amount of document report.
Document Journal of the American Chemical Society, 1975,97:6807-6810 are reported earliest super
Strong acid catalyst HF-SbF5On ethane and benzene alkylation reaction, the selectivity 76% of principal product ethylbenzene, but yield be only about
1%.Document Catalysis Letters, the ZSM-5 molecular sieve that 2001,73:175-180 reports the Pt load of 6.8wt% are urged
The alkylated reaction of ethane and benzene in agent, at 500 DEG C of reaction temperature, the conversion ratio of benzene is 8.3%, in addition there are ethylene and
Styrene generates, and the selectivity for providing each product is not known in document.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 and ethane mole
Than being 1/9, mass space velocity 3.1h-1When, in the alkylbenzene that ethane and benzene alkylation reaction generate, the selectivity of ethylbenzene is
92.6%, the selectivity of toluene is 0.99%, and the selectivity of diethylbenzene is 2.3%, but ethane conversion is lower than 2%.Above
In the document of open report, Pt/ZSM-5 molecular sieve catalyst is all made of to be supported on ZSM-5 molecular sieve for single Pt element,
It is seasonable for the alkylation between ethane and benzene, in the case where the parts by weight of precious metals pt element are more than or equal to 1%, ethane
It is still lower with the conversion ratio of benzene.
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 ethane and benzene
The problem that base answers the conversion ratio of middle benzene and ethane low provides the catalyst that one kind new ethane and benzene are alkylated reaction,
The catalyst has the advantages that the high conversion rate of ethane and benzene.
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 second using catalyst described in one of above-mentioned technical problem
Alkylation reaction method between alkane and benzene.
One of to solve above-mentioned technical problem, technical scheme is as follows: the catalysis of ethane and benzene alkylation reaction
Agent, including following components:
(a) Pt or its oxide；
(b) oxide of Zn；
(c) at least one of metal oxide in VIB or IIIA；
(d) molecular sieve.
In above-mentioned technical proposal, Zn element has with Pt element cooperates with facilitation.
In above-mentioned technical proposal, based on parts by weight, composition (a) is preferably 0.1~4 part, and more preferable 0.2~2 part.
In above-mentioned technical proposal, based on parts by weight, composition (b) is preferably 0.1~4 part, and more preferable 0.2~2 part.
In above-mentioned technical proposal, based on parts by weight, composition (c) is preferably 0.1~10 part, and more preferable 0.3~5 part.
In above-mentioned technical proposal, based on parts by weight, composition (d) is preferably 80~100 parts.
In above-mentioned technical proposal, the vib metal oxide preferably is selected from Cr2O3Or Mo2O3At least one of.
In above-mentioned technical proposal, the IIIA metal oxide preferably is selected from Ga2O3Or In2O3At least one of.
It most preferably simultaneously include vib metal element and IIIA metal, the vib metal is first at this time in above-mentioned technical proposal
There is synergistic effect, the synergistic effect between such as, but not limited to Cr and Ga between element and IIIA metallic element.
In above-mentioned technical proposal, the molecular sieve is hydrogen type molecular sieve.
In above-mentioned technical proposal, the molecular sieve is ZSM-5, Beta molecular sieve, MCM-22, ZSM-35, HMOR molecular sieve
At least one of.The Si/Al molar ratio of molecular sieve is not particularly limited, and those skilled in the art can reasonably select.Such as
But it is not limited to 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) 0.1~4 part of Pt or its oxide；
(b) oxide of 0.1~4 part of Zn；
(c) at least one of metal oxide in 0.1~10 part of VIB or IIIA；
(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:
It (1) will be containing the compound at least one of metal, the compound containing Pt in the VIB or IIIA and containing the compound of Zn
It is scattered in solvent；
(2) dispersion for obtaining step (1) impregnates the molecular sieve；
(3) it roasts.
In above-mentioned technical proposal, the compound containing Pt, the compound containing Zn contain and VIB or IIIA metallic element
Compound is not particularly limited, and those skilled in the art can reasonably select, such as the compound containing Pt can be but not
It is limited to chloroplatinic acid, four ammino platinum nitrates, the compound containing Zn but is not limited to zinc nitrate, zinc chloride, zinc acetate etc., it is described to contain
The compound of VIB or IIIA metallic element, such as, but not limited to nitrate, chloride etc..
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 optional 60~120 DEG C of drying temperature, does
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, and Zn element is with ZnO
Form exist, metallic element exists in the form of an oxide in VIB or IIIA, but uses the oxide preceding needed with reducing agent Pt
It is reduced to Pt metal；Or Pt element can exist in the form of Pt metal in the commercial form of the catalyst, Zn element is with ZnO
Form exist, metallic element exists in the form of an oxide in VIB or IIIA, at this time only in the preparation process of catalyst
Include the steps that reduction after roasting.Those skilled in the art will know that rationally determining actual reducing condition, such as but not
It is limited to: using pure hydrogen or hydrogen and inert gas mixture as reducing agent (such as, but not limited to hydrogen-nitrogen gaseous mixture, hydrogen
Gas-helium mix gas etc.).
To solve above-mentioned technical problem three, technical scheme is as follows: ethane and benzene are alkylated reaction
Method, in the presence of the catalyst described in any one of technical solution of one of above-mentioned technical problem, using ethane and benzene as raw material into
Row reaction obtains alkylate.
In above-mentioned technical proposal, reaction temperature is preferably 350~600 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 VIB or IIIA metallic element in Pt-Zn/ZSM-5 catalyst, improves the conversion of ethane and benzene
Rate especially has superior technique effect when containing VIB or IIIA metallic element simultaneously.Such as when using Pt-Zn-Cr-Ga/
When ZSM-5 is catalyst, for the high conversion rate of ethane up to 9.8%, benzene high conversion rate can be used for the base of ethane and benzene up to 28.3%
In reaction.
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), the zinc nitrate for being equivalent to 0.7g ZnO (divides
Minor is Zn (NO3)2·6H2O), it is equivalent to 1.1g Cr2O3Chromic nitrate (molecular formula be Cr (NO3)3·9H2O it) and is equivalent to
0.8g Ga2O3Gallium nitrate (molecular formula be Ga (NO3)3·9H2O it) is added in 120mL deionized water, stirring keeps it all molten
Solution forms mixed solution；The Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46) for weighing 96.9g, is then added to above-mentioned mixed
It closes in solution, impregnates 3h, 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 340 DEG C, and the recovery time is to obtain within 1 hour catalyst, and catalysis composition is shown in Table 1.
2, evaluating catalyst
Ethane and benzene alkylation reaction carry out on continuous fixed bed reactor, and Catalyst packing quality is 3.0g.
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-
485 DEG C of temperature, reaction pressure 0.1MPa are answered, the mass space velocity of raw material is 5.5h-1, the molar ratio of ethane and benzene is 6.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), the zinc nitrate for being equivalent to 0.7g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.9g Ga2O3Gallium nitrate (molecular formula be Ga (NO3)3·9H2O it) is added to
In 120mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-5 molecular sieve (Si/ of 96.9g
Al molar ratio is 46), to be then added in above-mentioned mixed solution, impregnates 3h, 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 340 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), the zinc nitrate for being equivalent to 0.7g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.9g Cr2O3Chromic nitrate (molecular formula be Cr (NO3)3·9H2O it) is added to
In 120mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-5 molecular sieve (Si/ of 96.9g
Al molar ratio is 46), to be then added in above-mentioned mixed solution, impregnates 3h, 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 340 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), the zinc nitrate for being equivalent to 0.7g ZnO (divides
Minor is Zn (NO3)2·6H2O), it is equivalent to 1.1g Cr2O3Chromic nitrate (molecular formula be Cr (NO3)3·9H2O it) and is equivalent to
0.8g In2O3Indium nitrate (molecular formula be In (NO3)3·5H2O it) is added in 120mL deionized water, stirring keeps it all molten
Solution forms mixed solution；The Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46) for weighing 96.9g, is then added to above-mentioned mixed
It closes in solution, impregnates 3h, 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 340 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), the zinc nitrate for being equivalent to 0.7g ZnO (divides
Minor is Zn (NO3)2·6H2O), it is equivalent to 0.8g Cr2O3Gallium nitrate (molecular formula be Cr (NO3)3·9H2O it) and is equivalent to
0.8g In2O3Indium nitrate (molecular formula be In (NO3)3·5H2O it) is added in 120mL deionized water, stirring keeps it all molten
Solution forms mixed solution；The Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 46) for weighing 97.2g, is then added to above-mentioned mixed
It closes in solution, impregnates 3h, 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 340 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 1.2g2PtCl6·6H2O), it is equivalent to 1.1g Cr2O3Chromic nitrate
(molecular formula is Cr (NO3)3·9H2O) and it is equivalent to 0.8g Ga2O3Gallium nitrate (molecular formula be Ga (NO3)3·9H2O it) is added to
In 120mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-5 molecular sieve (Si/ of 96.9g
Al molar ratio is 46), to be then added in above-mentioned mixed solution, impregnates 3h, 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 340 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 be equivalent to 1.2g ZnO zinc nitrate (molecular formula be Zn (NO3)2·6H2O), it is equivalent to 1.1g Cr2O3Nitre
(molecular formula is Cr (NO to sour chromium3)3·9H2O) and it is equivalent to 0.8g Ga2O3Gallium nitrate (molecular formula be Ga (NO3)3·9H2O) add
Enter into 120mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-5 molecular sieve of 96.9g
(Si/Al molar ratio is 46), is then added in above-mentioned mixed solution, impregnates 3h, 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 340 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 1 it is found that Cr and Ga is shown in terms of improving ethane and benzene conversion ratio compared with embodiment 2 and 3
Cooperate with facilitation.By embodiment 1 and comparative example 1 and 2 it is found that in terms of improving ethane and benzene conversion ratio Pt and the Zn list of elements
Reveal collaboration facilitation.
1 catalyst of table forms (indicating with weight percentage)
| Pt | ZnO | Cr2O3 | Ga2O3 | In2O3 | ZSM-5 | |
| Embodiment 1 | 0.5 | 0.7 | 1.1 | 0.8 | - | 96.9 |
| Embodiment 2 | 0.5 | 0.7 | - | 1.9 | - | 96.9 |
| Embodiment 3 | 0.5 | 0.7 | 1.9 | - | - | 96.9 |
| Embodiment 4 | 0.5 | 0.7 | 1.1 | 0.8 | 96.9 | |
| Embodiment 5 | 0.5 | 0.7 | - | 0.8 | 0.8 | 97.2 |
| Comparative example 1 | 1.2 | - | 1.1 | 0.8 | - | 96.9 |
| Comparative example 2 | - | 1.2 | 1.1 | 0.8 | - | 96.9 |
2 evaluating catalyst result of table
Claims (11)
1. the catalyst of ethane and benzene alkylation reaction, including following components:
(a) Pt or its oxide；
(b) oxide of Zn；
(c) vib metal oxide and IIIA metal oxide；
(d) molecular sieve,
Based on parts by weight, composition (a) is 0.1~4 part, and composition (b) is 0.1~4 part, and composition (c) is 0.1~10 part, composition
It (d) is 80~100 parts.
2. catalyst according to claim 1, it is characterized in that: the molecular sieve is hydrogen type molecular sieve.
3. catalyst according to claim 1, it is characterized in that: the molecular sieve be ZSM-5, Beta molecular sieve, MCM-22,
At least one of ZSM-35, HMOR molecular sieve.
4. catalyst according to claim 1, it is characterized in that: the vib metal oxide is selected from Cr2O3Or Mo2O3In
It is at least one.
5. catalyst according to claim 1, it is characterized in that: the IIIA metal oxide is selected from Ga2O3Or In2O3In
It is at least one.
6. the preparation method of catalyst described in claim 1, includes the following steps:
(1) by the compound containing the group vib metal, the compound containing the Group IIIA metal, the compound containing Pt and contain Zn
Compound be scattered in solvent；
(2) dispersion for obtaining step (1) impregnates the molecular sieve；
(3) it roasts.
7. the method for ethane and benzene alkylation reaction, using ethane and benzene as raw material, reaction is obtained containing second in the presence of a catalyst
The alkylbenzene of benzene, the catalyst includes following components:
(a) Pt or its oxide；
(b) oxide of Zn；
(c) at least one of metal oxide in VIB and IIIA；
(d) molecular sieve,
Based on parts by weight, composition (a) is 0.1~4 part, and composition (b) is 0.1~4 part, and composition (c) is 0.1~10 part, composition
It (d) is 80~100 parts.
8. according to the method described in claim 7, it is characterized in that: the molecular sieve is hydrogen type molecular sieve.
9. according to the method described in claim 7, it is characterized in that: the molecular sieve be ZSM-5, Beta molecular sieve, MCM-22,
At least one of ZSM-35, HMOR molecular sieve.
10. according to the method described in claim 7, it is characterized in that: the vib metal oxide is selected from Cr2O3Or Mo2O3In extremely
Few one kind.
11. according to the method described in claim 7, it is characterized in that: the IIIA metal oxide is selected from Ga2O3Or In2O3In
It is at least one.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1263480A (en) * | 1997-06-11 | 2000-08-16 | 戴姆勒-克莱斯勒股份公司 | Storage catalyst |
| CN1058476C (en) * | 1995-05-05 | 2000-11-15 | 陶氏化学公司 | Process of preparing ethylbenzene or substed. derivs. thereof |
| CN102451750A (en) * | 2010-10-21 | 2012-05-16 | 中国石油化工股份有限公司 | Selective dealkylation catalyst for alkyl aromatic hydrocarbon |
| CN103962172A (en) * | 2014-04-30 | 2014-08-06 | 上海倍能化工技术有限公司 | Method for preparing high-carbon hydrocarbon by using low-carbon oxygen containing compound as well as catalyst and preparation method thereof |
-
2015
- 2015-10-14 CN CN201510662113.2A patent/CN106582796B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1058476C (en) * | 1995-05-05 | 2000-11-15 | 陶氏化学公司 | Process of preparing ethylbenzene or substed. derivs. thereof |
| CN1263480A (en) * | 1997-06-11 | 2000-08-16 | 戴姆勒-克莱斯勒股份公司 | Storage catalyst |
| CN102451750A (en) * | 2010-10-21 | 2012-05-16 | 中国石油化工股份有限公司 | Selective dealkylation catalyst for alkyl aromatic hydrocarbon |
| CN103962172A (en) * | 2014-04-30 | 2014-08-06 | 上海倍能化工技术有限公司 | Method for preparing high-carbon hydrocarbon by using low-carbon oxygen containing compound as well as catalyst and preparation method thereof |
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