CN107282098B - The catalyst reacted for ethane with benzene - Google Patents
The catalyst reacted for ethane with benzene Download PDFInfo
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- CN107282098B CN107282098B CN201610223924.7A CN201610223924A CN107282098B CN 107282098 B CN107282098 B CN 107282098B CN 201610223924 A CN201610223924 A CN 201610223924A CN 107282098 B CN107282098 B CN 107282098B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
The present invention relates to a kind of catalyst reacted for ethane 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 present invention is by using the catalyst reacted for 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 in the production that ethane is reacted with benzene.
Description
Technical field
The present invention relates to a kind of catalyst reacted for benzene with ethane.
Background technique
Ethylbenzene is that the important commercialization derivative of benzene in current chemical industry has been also used to mainly for the production of styrene
Machine synthesis and intermediate pharmaceutically, can also make solvent use.Ethylbenzene yield is occupied quite big in basic organic chemical industry
Specific gravity, annual consumption is huge.Styrene is the important foundation raw material of petrochemical industry, mainly for the production of styrene series resin
And butadiene-styrene rubber, and production one of ion exchange resin and the raw material of pharmaceuticals.In addition, styrene can also be used in pharmacy, dye
The industries such as material, pesticide and ore dressing.The homopolymer polystyrene of styrene is one of five big general thermoplastic synthetic resins, extensively
For injection-molded item, extruded product and the big field of foamed product 3.And ethylbenzene is the critical materials for producing styrene, industrially
90% or more styrene is made by ethylbenzene.
Shale gas is a kind of important unconventional gas resource received significant attention in recent years.Shale gas great development makes
U.S.'s shale gas chemical industry is grown rapidly, and is established unique competitive advantage in global chemical industry at one stroke, is led to answering for U.S.'s chemical industry
It is emerging.The shale gas resource in China is very rich, and a large amount of ethane of association in shale gas, in natural gas, casing-head gas and refinery gas
Also cheap containing low-carbon alkanes such as a large amount of ethane.But ethane is highly stable due to structure, it is difficult to activate, be difficult conduct
The raw material of industry is directly applied.Ethane mainly passes through cracking to produce ethylene in chemical industry.Ethane will be blended in steam
It is cracked when 900 DEG C or more of high temperature, condition is harsh, energy consumption is high.Currently, being not yet able to achieve the work of ethane catalytic dehydrogenation
Industry metaplasia produces.Therefore, under temperate condition the Efficient Conversion of ethane be always catalytic field research difficult point and hot spot.
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 the alkane such as diethyl benzene,toluene,xylene can also be obtained
Base benzene.Ethylbenzene raw material sources can be widened in this way, are realized the lighting of raw material, are advantageously reduced production cost.Therefore, it utilizes
The alkylbenzenes such as ethane and one step alkylated reaction synthesizing ethyl benzene of benzene are realized with shale gas etc. as the large petrochemical industry of material downstream
The direct conversion of product 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, do not divided using SAPO-11 in the catalyst that is reacted for ethane with benzene
Son sieve, and only contain 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 reacted for 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) molecular sieve.
In above-mentioned technical proposal, the molecular sieve is at least one of ZSM-11, SAPO-11, MCM-22 molecular sieve.It is excellent
It selects while including at least one of ZSM-11, MCM-22 molecular sieve and SAPO-11 molecular sieve, ZSM-11, MCM-22 molecular sieve
At least one of between molecular sieve and SAPO-11 molecular sieve have synergistic effect, such as, but not limited to ZSM-11 molecular sieve with
SAPO-11 molecular sieve has synergistic effect in terms of improving ethane conversion.The most preferably described molecular sieve include simultaneously ZSM-11,
SAPO-11 and MCM-22, 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-11 molecular sieve, optional Si/Al molar ratio is 30~200；When using MCM-22 molecular sieve, optional Si/Al molar ratio
It is 50~200.
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-Nd/ molecular sieve catalyst simultaneously
When comprising MCM-22, ZSM-11 and SAPO-11, three kinds of molecular sieves have mutual promoting action, and the high conversion rate of ethane reaches
15.6%, the conversion ratio of benzene can be used in the reacting of ethane and benzene up to 21.7%.
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 1.5g2PtCl6·6H2O), the zinc nitrate for being equivalent to 1.4g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.0g Nd2O3Neodymium nitrate (molecular formula be Nd (NO3)3·6H2O it) is added to
In 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-11 molecular sieve of 37.23g
The Hydrogen SAPO-11 molecular sieve (Si/P/Al molar ratio is 0.32:1:1) of (Si/Al molar ratio is 90) and 59.69g, 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
Benzene carries out on continuous fixed bed reactor with ethane alkylated reaction, and Catalyst packing quality is 2.0g.
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-
550 DEG C of temperature, reaction pressure 0.1MPa are answered, the mass space velocity of raw material is 4.0h-1, the molar ratio of ethane and benzene is 4.2.Reaction
It the results are shown in Table 2.
[embodiment 2]
1, catalyst preparation
Weigh chloroplatinic acid (the molecular formula H of the Pt containing 1.5g2PtCl6·6H2O), the zinc nitrate for being equivalent to 1.4g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.0g Nd2O3Neodymium nitrate (molecular formula be Nd (NO3)3·6H2O it) is added to
In 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-11 molecular sieve of 37.23g
The Hydrogen MCM-22 molecular sieve (Si/Al molar ratio is 78) of (Si/Al molar ratio is 90) and 37.23g, 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 1.5g2PtCl6·6H2O), the zinc nitrate for being equivalent to 1.4g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.0g Nd2O3Neodymium nitrate (molecular formula be Nd (NO3)3·6H2O it) is added to
In 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen MCM-22 molecular sieve of 37.23g
The Hydrogen SAPO-11 molecular sieve (Si/P/Al molar ratio is 0.32:1:1) of (Si/Al molar ratio is 78) and 59.69g, 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 1.5g2PtCl6·6H2O), the zinc nitrate for being equivalent to 1.4g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.0g Nd2O3Neodymium nitrate (molecular formula be Nd (NO3)3·6H2O it) is added to
In 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen MCM-22 molecular sieve of 13.75g
(Si/Al molar ratio is 78), weigh 37.23g Hydrogen ZSM-11 molecular sieve (Si/Al molar ratio is 90) and 59.69g Hydrogen
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 1.5g2PtCl6·6H2O), the zinc nitrate for being equivalent to 1.4g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.0g Nd2O3Neodymium nitrate (molecular formula be Nd (NO3)3·6H2O it) is added to
In 160mL deionized water, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen SAPO-11 molecular sieve of 96.92g
(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 1.5g2PtCl6·6H2O), the zinc nitrate for being equivalent to 1.4g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.0g Nd2O3Neodymium nitrate (molecular formula be Nd (NO3)3·6H2O it) is added to
In the deionized water of 160mL, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen ZSM-11 molecular sieve of 37.23g
(Si/Al molar ratio is 90), 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 1.5g2PtCl6·6H2O), the zinc nitrate for being equivalent to 1.4g ZnO (divides
Minor is Zn (NO3)2·6H2O) and it is equivalent to 1.0g Nd2O3Neodymium nitrate (molecular formula be Nd (NO3)3·6H2O it) is added to
In the deionized water of 160mL, stirring dissolves it all, forms mixed solution；Weigh the Hydrogen MCM-22 molecular sieve of 96.92g
(Si/Al molar ratio is 78), 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-11 or
It shows to cooperate with facilitation between MCM-22 molecular sieve and SAPO-11 molecular sieve.
By embodiment 1, embodiment 3 compared with embodiment 4 it is found that molecular sieve include simultaneously ZSM-11, SAPO-11 and
When MCM-22, three with mutually in terms of improving ethane conversion have facilitation.
1 catalyst of table forms (indicating with weight percentage)
| Pt | ZnO | Nd2O3 | SAPO-11 | MCM-22 | ZSM-11 | Molecular sieve | |
| Embodiment 1 | 1.5 | 1.4 | 1.0 | 46.5 | 49.6 | - | 96.1 |
| Embodiment 2 | 1.5 | 1.4 | 1.0 | - | 46.5 | 49.6 | 96.1 |
| Embodiment 3 | 1.5 | 1.4 | 1.0 | 49.6 | - | 49.6 | 96.1 |
| Embodiment 4 | 1.5 | 1.4 | 1.0 | 49.6 | 19.3 | 30.3 | 96.1 |
| Embodiment 6 | 1.5 | 1.4 | 1.0 | 96.1 | - | - | 96.1 |
| Embodiment 7 | 1.5 | 1.4 | 1.0 | - | 96.1 | - | 96.1 |
| Embodiment 8 | 1.5 | 1.4 | 1.0 | - | - | 96.1 | 96.1 |
2 evaluating catalyst result of table
Claims (5)
1. for the catalyst that ethane is reacted with benzene, including following components:
(a) Pt or its oxide, based on parts by weight, composition (a) are 0.1~4 part；
(b) oxide of Zn, based on parts by weight, composition (b) are 0.1~5 part；
(c) simple substance or oxide of La series elements, based on parts by weight, composition (c) are 0.08~5 part；
(d) molecular sieve, based on parts by weight, composition (d) are 80~100 parts；
Wherein, the molecular sieve includes simultaneously at least one of ZSM-11, MCM-22 molecular sieve and SAPO-11 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.
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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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2016
- 2016-04-12 CN CN201610223924.7A patent/CN107282098B/en active Active
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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