CN107282090B - The catalyst that ethane is reacted with benzene - Google Patents
The catalyst that ethane is reacted with benzene Download PDFInfo
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Abstract
The present invention relates to the catalyst that ethane is reacted with benzene, 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, the catalyst that the present invention is reacted by using ethane with benzene, including following components: (a) Pt or its oxide；(b) oxide of Zn；(c) simple substance or oxide of La series elements；(d) technical solution of molecular sieve preferably solves the technical problem, can be used for during ethane reacts with benzene.
Description
Technical field
The present invention relates to a kind of catalyst reacted for ethane with benzene.
Background technique
Shale gas is a kind of important unconventional gas resource received significant attention in recent years.U.S.'s shale gas chemical industry
Cost advantage it is obvious, the adverse effect of China's oil chemical industry can not be ignored, the development and utilization of shale gas, it has also become low
The catalyst of important impetus and the world's oil-gas geopolitics configuration structure adjustment of carbon economic strategy opportunity to develop.China
Shale gas resource is very rich, and a large amount of ethane of association in shale gas, also containing a large amount of in natural gas, casing-head gas and refinery gas
The low-carbon alkanes such as ethane, it is cheap.But ethane is highly stable due to structure, it is difficult to activate, be difficult straight as the raw material of industry
Scoop out use.Ethane mainly passes through cracking to produce ethylene in chemical industry.Ethane will be blended in 900 DEG C or more with steam
High temperature when cracked, condition is harsh, energy consumption is high.Currently, being not yet able to achieve the industrialized production of ethane catalytic dehydrogenation.Cause
This, the Efficient Conversion of ethane is always the difficult point and hot spot of catalytic field research under temperate condition.
In recent years, foreign literature proposes a kind of new method using low-carbon alkanes such as ethane, and ethane and benzene are carried out alkane
Glycosylation reaction, can synthesizing ethyl benzene at relatively low temperature, while it is more to obtain diethyl benzene,toluene,xylene etc.
Kind alkylbenzene.Wherein, ethylbenzene is one of most important commercialization derivative of benzene in current chemical industry, mainly for the production of benzene second
Alkene is also used to organic synthesis and intermediate pharmaceutically, can also make solvent use.Ethylbenzene yield is in basic organic chemical industry
Occupy sizable specific gravity, annual consumption is huge.Styrene is the important foundation raw material of petrochemical industry, mainly for the production of benzene second
Alkene series plastics and butadiene-styrene rubber, and production one of ion exchange resin and the important source material of pharmaceuticals.In addition, styrene is also
It can be used for the industries such as pharmacy, dyestuff, pesticide and ore dressing.And ethylbenzene be produce styrene critical materials, industrial 90% with
On styrene be made by ethylbenzene.So having expanded original using the alkylbenzenes such as ethane and one step alkylated reaction synthesizing ethyl benzene of benzene
Expect source, may be implemented that there is great research using shale gas as the direct conversion of the large petrochemicals of material downstream
Meaning 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, without using SAPO-11 molecular sieve in the catalyst that ethane is reacted with benzene,
And only containing a kind of molecular sieve, the conversion ratio of ethane and benzene is lower.
Summary of the invention
The first technical problem to be solved by the present invention be molecular sieve carried Pt catalyst for ethane reacted with benzene in second
The low problem of the conversion ratio of alkane, provides a kind of catalyst that new ethane is reacted with benzene, which has ethane conversion high
The advantages of.
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
The method that alkane is reacted with benzene.
One of to solve above-mentioned technical problem, technical scheme is as follows: the catalyst that ethane is reacted with benzene, including
Following components:
(a) Pt or its oxide；
(b) oxide of Zn；
(c) simple substance or oxide of La series elements；
(d) molecular sieve.
In above-mentioned technical proposal, the molecular sieve is at least one of Beta, SAPO-11, ZSM-5 molecular sieve.It is preferred that
It simultaneously include at least one of ZSM-5, Beta molecular sieve and SAPO-11 molecular sieve, at least one in ZSM-5, Beta molecular sieve
There is synergistic effect, such as, but not limited to ZSM-5 molecular sieve and SAPO-11 molecule between kind molecular sieve and SAPO-11 molecular sieve
Sieve has synergistic effect in terms of improving ethane conversion.The most preferably described molecular sieve include simultaneously ZSM-5, SAPO-11 and
Beta, three has mutual promoting action in terms of improving ethane conversion at this time.
In above-mentioned technical proposal, based on parts by weight, composition (a) is preferably 0.1~4 part, and more preferable 0.5~2 part.
In above-mentioned technical proposal, based on parts by weight, composition (b) is preferably 0.1~5 part, and more preferable 0.25~2 part.
In above-mentioned technical proposal, based on parts by weight, composition (c) is preferably 0.08~5 part, and more preferable 0.2~2 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, Nd and Eu.
In above-mentioned technical proposal, the molecular sieve is hydrogen type molecular sieve.
The Si/P/Al molar ratio or Si/Al molar ratio of molecular sieve are not particularly limited, and those skilled in the art can be reasonable
Selection.Such as, but not limited to when using SAPO-11 molecular sieve, optional Si/P/Al molar ratio is (0.2-2): 1:1；Work as use
When ZSM-5 molecular sieve, optional Si/Al molar ratio is 20~300；When using Beta molecular sieve, optional Si/Al molar ratio is 50
~300.
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 Zn 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 Zn are not particularly limited, this field skill
Art personnel can reasonably select, such as the compound containing Pt can be but not limited to chloroplatinic acid, four ammino platinum nitrates, described
Compound containing Zn but it is not limited to zinc nitrate, zinc chloride, zinc acetate etc., the compound of the series elements containing La, for example (,) but it is unlimited
In 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
Directly to dissolve, or by adjusting pH dissolution, being also possible to that colloid can be formed or forming that of colloid by adjusting pH
A little solvents 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 element can exist in the form of an oxide in the commercial form of the catalyst, Zn element
Exist in the form of ZnO, but using preceding needing that the oxide of Pt is reduced to Pt metal with reducing agent；Or the catalyst
Pt element can exist in the form of Pt metal in commercial form, and Zn element exists in the form of ZnO, at this time only in catalyst
Include the steps that reduction in preparation process after firing.Those skilled in the art will know that rationally determining actual reduction item
Part, such as, but not limited to: using pure hydrogen or hydrogen and inert gas mixture as reducing agent (such as, but not limited to hydrogen-nitrogen
Gas gaseous mixture, hydrogen-helium mix gas etc.).
To solve above-mentioned technical problem three, technical scheme is as follows: the method that ethane is reacted with benzene, above-mentioned
In the presence of catalyst described in any one of technical solution of one of technical problem, reacted to obtain alkane as raw material using benzene and ethane
Base product.
In above-mentioned technical proposal, reaction temperature is preferably 400~580 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 contains SAPO-11 molecular sieve in Pt-Zn-Ce/ molecular sieve catalyst, and at least containing there are two types of molecules
Sieve, in ethane is reacted with benzene, improves the conversion ratio of ethane and benzene.Such as when in Pt-Zn-La/ molecular sieve catalyst simultaneously
When comprising Beta, ZSM-5 and SAPO-11, three kinds of molecular sieves have a mutual promoting action, the high conversion rate of ethane up to 16.2%,
The conversion ratio of benzene can be used in ethane alkylated reaction up to 24.2%.
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 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-5 molecular sieve of 46.19g
The Hydrogen SAPO-11 molecular sieve (Si/P/Al molar ratio is 0.32:1:1) of (Si/Al molar ratio is 100) and 50.35g, then
It is add to the above mixed solution, 80 DEG C of dippings 5h, 100 DEG C of dry 12h, 500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 is reacted with benzene to carry out on continuous fixed bed reactor, and Catalyst packing quality is 2.0g.Before reaction,
Then temperature of reactor is adjusted to reaction temperature, is passed through feed ethan and is reacted with benzene.Reaction condition are as follows: reaction temperature
545 DEG C, reaction pressure 0.12MPa, the mass space velocity of raw material is 4.2h-1, the molar ratio of ethane and benzene is 4.5.Reaction result
It is shown in Table 2.
[embodiment 2]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-5 molecular sieve of 46.19g
The Hydrogen Beta molecular sieve (Si/Al molar ratio is 96) of (Si/Al molar ratio is 100) and 50.35g, are then added to above-mentioned
In mixed solution, 80 DEG C of dippings 5h, 100 DEG C of dry 12h, 500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 reactivity worth 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 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen Beta molecular sieve of 46.19g
The Hydrogen SAPO-11 molecular sieve (Si/P/Al molar ratio is 0.32:1:1) of (Si/Al molar ratio is 96) and 50.35g, then
It is add to the above mixed solution, 80 DEG C of dippings 5h, 100 DEG C of dry 12h, 500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 reactivity worth 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 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g Eu2O3Europium nitrate (molecular formula be Eu (NO3)3·6H2O it) is added
Into 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen Beta molecular sieve of 17.88g
The Hydrogen of Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 100) and 50.35g of (Si/Al molar ratio is 96), 28.31g
SAPO-11 molecular sieve (Si/P/Al molar ratio is 0.32:1:1), is then add to the above mixed solution, 80 DEG C of dipping 5h,
100 DEG C of dry 12h, 500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 reactivity worth 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 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen Beta molecular sieve of 17.88g
The Hydrogen of Hydrogen ZSM-5 molecular sieve (Si/Al molar ratio is 100) and 50.35g of (Si/Al molar ratio is 96), 28.31g
SAPO-11 molecular sieve (Si/P/Al molar ratio is 0.32:1:1), is then add to the above mixed solution, 80 DEG C of dipping 5h,
100 DEG C of dry 12h, 500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 reactivity worth are evaluated according to the same manner as in Example 1.Reaction result is shown in Table 2.
[embodiment 6]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen SAPO-11 molecular sieve of 96.54g
(Si/P/Al molar ratio is 0.32:1:1), is then added in above-mentioned mixed solution, 80 DEG C of dippings 5h, 100 DEG C of dry 12h,
500 DEG C of roasting 2h.
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 reactivity worth are evaluated according to the same manner as in Example 1.Reaction result is shown in Table 2.
[embodiment 7]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into the deionized water of 160mL, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-5 molecular sieve of 96.54g
(Si/Al molar ratio is 100), is then added in above-mentioned mixed solution, 80 DEG C of dippings 5h, 100 DEG C of dry 12h, 500 DEG C of roastings
2h。
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 reactivity worth are evaluated according to the same manner as in Example 1.Reaction result is shown in Table 2.
[embodiment 8]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 1.33g2PtCl6·6H2O), it is equivalent to the zinc nitrate of 1.15g ZnO
(molecular formula is Zn (NO3)2·6H2O) and it is equivalent to 0.98g La2O3Lanthanum nitrate (molecular formula be La (NO3)3·6H2O it) is added
Into the deionized water of 160mL, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen Beta molecular sieve of 96.54g
(Si/Al molar ratio is 96), is then added in above-mentioned mixed solution, 80 DEG C of dippings 5h, 100 DEG C of dry 12h, 500 DEG C of roastings
2h。
Above-mentioned product tabletting is crushed to 40~60 mesh, uses the hydrogen volume content to be for 5% hydrogen-nitrogen gaseous mixture
Reducing agent, reduction temperature are 325 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 reactivity worth are evaluated according to the same manner as in Example 1.Reaction result is shown in Table 2.
By embodiment 1, embodiment 3 compared with comparative example it is found that in terms of improving ethane and benzene conversion ratio ZSM-5 or
It shows to cooperate with facilitation between Beta molecular sieve and SAPO-11 molecular sieve.
By embodiment 1, embodiment 3 compared with embodiment 5 it is found that molecular sieve include simultaneously ZSM-5, SAPO-11 and
When Beta, three has mutual promoting action in terms of improving ethane and benzene conversion ratio.
1 catalyst of table forms (indicating with weight percentage)
| Pt | ZnO | La2O3 | Eu2O3 | SAPO-11 | ZSM-5 | Beta | Molecular sieve | |
| Embodiment 1 | 1.33 | 1.15 | 0.98 | - | 50.35 | 46.19 | - | 96.54 |
| Embodiment 2 | 1.33 | 1.15 | 0.98 | - | - | 46.19 | 50.35 | 96.54 |
| Embodiment 3 | 1.33 | 1.15 | 0.98 | - | 50.35 | - | 46.19 | 96.54 |
| Embodiment 4 | 1.33 | 1.15 | - | 0.98 | 50.35 | 28.31 | 17.88 | 96.54 |
| Embodiment 5 | 1.33 | 1.15 | 0.98 | - | 50.35 | 28.31 | 17.88 | 96.54 |
| Embodiment 6 | 1.33 | 1.15 | 0.98 | - | 96.54 | - | - | 96.54 |
| Embodiment 7 | 1.33 | 1.15 | 0.98 | - | - | 96.54 | - | 96.54 |
| Embodiment 8 | 1.33 | 1.15 | 0.98 | - | - | - | 96.54 | 96.54 |
2 evaluating catalyst result of table
Claims (5)
1. the catalyst that ethane is reacted with benzene, based on parts by weight, including following components:
(a) 0.1~4 part of Pt or its oxide；
(b) oxide of 0.1~5 part of Zn；
(c) simple substance or oxide of 0.08~5 part of La series elements；
(d) 80~100 parts of molecular sieves,
The molecular sieve is at least one of SAPO-11 molecular sieve and ZSM-5 or Beta molecular sieve.
2. catalyst according to claim 1, characterized in that the La series elements in La, Ce, Pr and Nd at least
It is a kind of.
3. catalyst according to claim 1, it is characterized in that: the molecular sieve is hydrogen type molecular sieve.
4. the preparation method of catalyst described in claim 1, includes the following steps:
(1) it disperses the compound containing Pt, the compound containing Zn and the compound containing the La series elements in solvent；
(2) dispersion for obtaining step (1) impregnates the molecular sieve；
(3) it roasts.
5. the method that ethane is reacted with benzene, using ethane and benzene as raw material, the catalyst described in any one of claims 1 to 3 is deposited
In lower reaction, based on parts by weight, composition includes: the composition of the catalyst
(a) 0.1~4 part of Pt or its oxide；
(b) oxide of 0.1~5 part of Zn；
(c) simple substance or oxide of 0.08~5 part of La series elements；
(d) 80~100 parts of molecular sieves,
The molecular sieve is at least one of SAPO-11 molecular sieve and ZSM-5 or Beta molecular sieve.
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Citations (3)
| 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 |
| CN104148104A (en) * | 2013-05-16 | 2014-11-19 | 中国石油化工股份有限公司 | Catalyst and method of cracked gasoline hydrogenation |
| CN106582791A (en) * | 2015-10-14 | 2017-04-26 | 中国石油化工股份有限公司 | Catalyst for producing ethylbenzene from benzene and ethane |
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Patent Citations (3)
| 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 |
| CN104148104A (en) * | 2013-05-16 | 2014-11-19 | 中国石油化工股份有限公司 | Catalyst and method of cracked gasoline hydrogenation |
| CN106582791A (en) * | 2015-10-14 | 2017-04-26 | 中国石油化工股份有限公司 | Catalyst for producing ethylbenzene from benzene and ethane |
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