CN108689790A - A method of cyclopentene is prepared by Selective Hydrogenation of Cyclopentadiene - Google Patents
A method of cyclopentene is prepared by Selective Hydrogenation of Cyclopentadiene Download PDFInfo
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- CN108689790A CN108689790A CN201710224457.4A CN201710224457A CN108689790A CN 108689790 A CN108689790 A CN 108689790A CN 201710224457 A CN201710224457 A CN 201710224457A CN 108689790 A CN108689790 A CN 108689790A
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- catalyst
- cyclopentadiene
- selective hydrogenation
- cyclopentene
- acetate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
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Abstract
The present invention provides a kind of methods preparing cyclopentene by Selective Hydrogenation of Cyclopentadiene, including:After cyclopentadiene, hydrogen gas, liquid diluent and conditioning agent are mixed, selective hydrogenation reaction is carried out in the presence of nickel-copper base catalyst, prepares cyclopentene, wherein the conditioning agent is carbon monoxide.For Selective Hydrogenation of Cyclopentadiene technique, the catalyst, conditioning agent, esters liquid phase diluent collective effect under, overcome the shortcomings of reaction heat in the prior art is difficult to removal in time, reaction selectivity is poor, catalyst life is short, cyclopentene can be prepared with high selectivity, catalyst activity is high, stability is high, and catalyst life greatly prolongs, at the same can also the impurity such as sulfur resistive and arsenic catalyst is poisoned.
Description
Technical field
The present invention relates to cyclopentene preparation fields, and in particular to a kind of side preparing cyclopentene by Selective Hydrogenation of Cyclopentadiene
Method.
Background technology
Cyclopentene is a kind of important Organic Chemicals, can be widely applied to pharmaceuticals industry, organic synthesis, synthetic rubber
And field of fine chemical.Can thus be that raw material prepares cyclopentanol, ring valeric acid, ring penta since cyclopentene has activated double bonds
The high added values medicine intermediate such as ketone, bromocyclopentane;In addition, cyclopentene prepares the important source material of polycyclic amylene rubber.
In the prior art, cyclopentene can be obtained by a variety of methods, however in the method for the production of Selective Hydrogenation of Cyclopentadiene
Most industrial prospect.But it selects in hydrogenation process, cyclopentadiene easily generates pentamethylene by complete hydrogenation, due to pentamethylene
It is closer to the boiling point of cyclopentene, it is difficult to detach, therefore, if highly selective generation cyclopentene is evaluation catalyst and technique
The key index of condition quality.In addition, there is also the segregation ratio of catalyst and cyclopentene for the preparation method of existing cyclopentadiene
It is more difficult, it is difficult to the shortcomings of removing low reaction heat, reaction product yield, poor selectivity in time.Even if higher using cost
Noble metal, drawbacks described above also not be improved significantly.
Invention content
In view of the deficiencies of the prior art, the present invention is intended to provide a kind of side preparing cyclopentene by Selective Hydrogenation of Cyclopentadiene
Method, by being carried out using specific catalyst, liquid phase diluent and tune in selective hydrogenation by cyclopentadiene and hydrogen
Save agent, can significantly improve the activity, selectivity and stability of catalyst, especially make catalyst service life and the service life significantly
Increase.
Therefore, the purpose of the present invention is to provide a kind of methods preparing cyclopentene by Selective Hydrogenation of Cyclopentadiene, including:
After cyclopentadiene, hydrogen gas, liquid diluent and conditioning agent are mixed, selection plus hydrogen are carried out in the presence of nickel-copper base catalyst
Reaction, prepares cyclopentene;Wherein, the conditioning agent is carbon monoxide (CO).
The technique that present inventor prepares Selective Hydrogenation of Cyclopentadiene cyclopentene has carried out research extensively and profoundly,
As a result, it has been found that CO is capable of the activity of Reasonable Regulation And Control catalyst when with nickel-copper base catalyst and conditioning agent cooperation, so as to
The phenomenon that avoiding in conversion zone quick release a large amount of reaction heat, and reaction heat is thus caused to be difficult to remove in time not
Foot, and then the selectivity of reaction product and the stability of catalyst can be substantially improved, and using the technical method to ring penta
When diene selection hydrogenation prepares cyclopentene, the service life of catalyst and service life also greatly increase, and increase up to one times or more.Hair
It is bright be based on it is above discovery be accomplished.
In the preferred embodiment of the present invention, the nickel-copper base catalyst includes the nickel being supported on carrier
And copper, and optionally contain and help active metal.
According to the present invention, described one kind for helping active metal in Li, Na, K, Cs, Ca, Mg, Ba, La, Ce, Nd and Zn
Or it is a variety of, it is preferably one or more in K, Mg, Ba and Cs.According to the present invention, the carrier is that titanium dioxide-aluminum oxide is compound
Material.Preferably, the surface area of the titanium dioxide-aluminum oxide composite material (before load active component) is 120-150m2/ g,
Kong Rongwei 0.5-1.0ml/g, most probable pore size 10-14nm.In addition, the shape of titanium dioxide-aluminum oxide composite material is without spy
Different limitation, such as can be spherical shape, cloverleaf pattern, cylindricality, bar shaped, zigzag, preferably cloverleaf pattern.
According to the present invention, the titanium dioxide-aluminum oxide composite material can be prepared by the method for this field routine, such as
It can be prepared according to method disclosed in Chinese patent CN1184289C.
According to the present invention, in the titanium dioxide-aluminum oxide composite carrier, the content of titanium oxide is based on alumina weight
3-25wt%, preferably 5-20wt%, more preferably 6-16wt%.
It, can will be as the nickel of catalytically-active metals component and copper, Yi Jike in order to obtain the catalyst used in the present invention
That selects helps active metal by means commonly known in the art, such as dipping, co-precipitation, cogelledization or ion exchange, once or divides
Being dispersed on the titanium dioxide-aluminum oxide composite carrier for batch, is urged by calcining again after generally use infusion process
Agent presoma.
It is possible to further be activated with hydrogen reducing to loaded catalyst presoma, in order to realize the reduction activation
Journey is usually 8-16L/min in 100-180 DEG C of temperature, Hydrogen Vapor Pressure 1.5-3.5MPa and per volume of catalyst hydrogen flowing quantity
Under conditions of kept for 3-8 hours.
Alternatively, it is also possible to select not carry out catalyst precursor special hydrogen reducing activation, work as catalyst precursors
When for being catalyzed Selective Hydrogenation of Cyclopentadiene reaction, in catalytic reaction process, the active component of catalyst also can be gradually by oxygen
Change state and be reduced to metal simple-substance form, equally can also achieve the purpose that activated catalyst.
It is in terms of 100% by the total weight of catalyst, the content of nickel is in the preferred embodiment of the present invention
1-30wt%, preferably 3-25wt%, more preferably 4-20wt%;The content of copper is 0.1-8wt%;Help the content of active metal
For 0-3wt%, preferably 0-2.0wt%, more preferably 0.01-1.0wt%.
In another preferred embodiment of the present invention, the liquid phase diluent is ester type compound, preferably first
Sour methyl esters, butyl formate, ethyl acetate, butyl acetate, isopropyl acetate, sec-butyl acetate, pentyl acetate, isoamyl acetate,
It is one or more in methyl amyl acetate, n-butyl propionate, isopropyl acetoacetate and ethyl acetoacetate, more preferably second
It is one or more in acetoacetic ester, pentyl acetate and ethyl acetoacetate.
In another preferred embodiment of the present invention, the molar ratio of the carbon monoxide and hydrogen is 1:(20-
100), preferably 1:(30-80), more preferably 1:(40-70).
In another preferred embodiment of the present invention, the molar ratio of the hydrogen and cyclopentadiene is (0.5-8):
1, preferably (1-5):1, more preferably (1.2-3.0):1.
In another preferred embodiment of the present invention, the weight ratio of the cyclopentadiene and liquid phase diluent is 1:
(5-10);Catalyst loading is 3-20h-1, preferably 5-15h-1。
In another preferred embodiment of the present invention, the temperature of the selective hydrogenation reaction is 0-150 DEG C, preferably
It is 15-100 DEG C, more preferably 40-100 DEG C;Reaction pressure is 0.1-5.0MPa, preferably 0.5-3.0MPa.
In the specific embodiment of the present invention, make using CO as conditioning agent using pentyl acetate as liquid phase diluent
Pentyl acetate, cyclopentadiene, hydrogen and CO enter after being mixed in the oil-gas mixer at reactor inlet is filled with nickel-copper base
It it is 40-100 DEG C in hydrogenation temperature, Hydrogen Vapor Pressure is the reaction of 0.5-3.0MPa in the reactor of the catalyst bed of catalyst
Under the conditions of, selective hydrogenation reaction occurs for cyclopentadiene, and generation includes the reaction product of cyclopentene, and reaction product is gone out from reactor
Material mouth is discharged.Feeding is sent to gas-chromatography and carries out composition analysis, other enter centrifugal station.
For the Selective Hydrogenation of Cyclopentadiene technique of the present invention, in the catalyst, conditioning agent CO, the dilution of esters liquid phase
Under the collective effect of agent, reaction heat in the prior art is difficult to removal in time, reaction selectivity is poor, catalyst life is short etc. is overcome
Disadvantage can prepare cyclopentene with high selectivity using the technique of the present invention, and catalyst activity is high, and stability is high, the catalyst longevity
Life greatly prolongs, at the same can also the impurity such as sulfur resistive and arsenic catalyst is poisoned.
Description of the drawings
Fig. 1 is the process flow chart of embodiment 1.
Specific implementation mode
The present invention is further described with embodiment below, it is noted that these embodiments are exemplary only,
The spirit and scope of the present invention are not limited in any way.
Reactor is fixed bed reactors, and the position of material inlet and outlet is not limited to as shown in the figure.Catalyst fills
It is 200ml to fill out volume, and cyclopentadiene raw material used is obtained by commercial channel, and hydrogen, which is tube hydrogen, CO is commercially available obtains
.In the following embodiments, the definition of catalyst loading, conversion ratio and selectivity is:
When cyclopentadiene conversion ratio is less than 85%, and cyclopentene is selectively less than 90%, Catalyst Definitions are failure.Catalysis
The agent service life refers to that catalyst is kept for the time of non-failure state.
Embodiment 1
For catalyst using titanium dioxide-aluminum oxide composite material as carrier, nickel-copper is active component, the gross weight based on catalyst
Amount, nickel content 15wt%, copper content 3.8wt%, it is 0.5wt% to help the content of active metal K.Make pentyl acetate, ring penta
Diene, hydrogen and CO enter the catalysis for being filled with nickel-copper base catalyst after being mixed in the oil-gas mixer at reactor inlet
In the reactor of agent bed, under the reaction conditions shown in Table 1, selection plus hydrogen occur for cyclopentadiene, and generation includes cyclopentene
Reaction product, by reaction product from reactor discharge port be discharged.Feeding is sent to gas-chromatography and carries out composition analysis, other entrance
Centrifugal station.
Embodiment 2
For catalyst using titanium dioxide-aluminum oxide composite material as carrier, nickel-copper is active component, the gross weight based on catalyst
The content of amount, nickel content 10wt%, copper is 8wt%.Selective hydrogenation reaction, specific work are carried out in the way of embodiment 1
Skill condition and reaction result are as shown in table 1.
Embodiment 3
For catalyst using titanium dioxide-aluminum oxide composite material as carrier, nickel-copper is active component, the gross weight based on catalyst
The content of amount, nickel content 15wt%, copper is 0.2wt%, and it is 0.5wt% to help the content of active metal Mg.According to embodiment 1
Mode carries out selective hydrogenation reaction, and specific process conditions and reaction result are as shown in table 1.
Embodiment 4
For catalyst using titanium dioxide-aluminum oxide composite material as carrier, nickel-copper is active component, the gross weight based on catalyst
The content of amount, nickel content 15wt%, copper is 5wt%, and it is 0.6wt% to help the content of active metal Ba.According to the side of embodiment 1
Formula carries out selective hydrogenation reaction, and specific process conditions and reaction result are as shown in table 1.
Embodiment 5
For catalyst using titanium dioxide-aluminum oxide composite material as carrier, nickel-copper is active component, the gross weight based on catalyst
Amount, nickel content 15wt%, copper content 3.8wt%, it is 0.5wt% to help the content of active metal Cs.According to the side of embodiment 1
Formula carries out selective hydrogenation reaction, and specific process conditions and reaction result are as shown in table 1.
Embodiment 6
The catalyst provided using embodiment 1, carries out selective hydrogenation reaction, specific technique in the way of embodiment 1
Condition and reaction result are as shown in table 1.
Embodiment 7
For catalyst using titanium dioxide-aluminum oxide composite material as carrier, nickel-copper is active component, the gross weight based on catalyst
Amount, nickel content 20wt%, copper content 3wt%, it is 0.3wt% to help the content of active metal K.In the way of embodiment 1
Selective hydrogenation reaction is carried out, specific process conditions and reaction result are as shown in table 1.
Embodiment 8
For catalyst using titanium dioxide-aluminum oxide composite material as carrier, nickel-copper is active component, the gross weight based on catalyst
Amount, nickel content 4wt%, copper content 8wt%, to help active metal K contents be 0.5wt%, is selected in the way of embodiment 1
Hydrogenation reaction is selected, specific process conditions and reaction result are as shown in table 1.
Comparative example 1
The catalyst provided using embodiment 1, and selective hydrogenation reaction, difference are carried out in the way of embodiment 1
It is, liquid phase diluent is normal octane, and does not use carbon monoxide conditioning agent, specific process conditions and reaction result such as table 1
It is shown.
Comparative example 2
The catalyst provided using embodiment 1, and selective hydrogenation reaction, difference are carried out in the way of embodiment 1
It is, the molar ratio of carbon monoxide conditioning agent and hydrogen is 1:18, specific process conditions and reaction result are as shown in table 1.
Comparative example 3
The catalyst provided using embodiment 1, and selective hydrogenation reaction, difference are carried out in the way of embodiment 1
It is, the molar ratio of carbon monoxide conditioning agent and hydrogen is 1:110, specific process conditions and reaction result are as shown in table 1.
Although the present invention has been described in detail, it will be understood by those skilled in the art that in spirit and scope of the invention
Modification will be apparent.However, it should be understood that various aspects, different specific implementation mode that the present invention records
Each section and the various features enumerated can be combined or all or part of exchange.In above-mentioned each specific implementation mode, that
A little embodiments with reference to another embodiment can be combined suitably with other embodiment, this is will be by this field skill
Art personnel are to understand.In addition, it will be understood to those of skill in the art that the description of front is only exemplary mode, not purport
In the limitation present invention.
Claims (10)
1. a kind of method that cyclopentene is prepared by Selective Hydrogenation of Cyclopentadiene, including:By cyclopentadiene, hydrogen gas, liquid diluent
After being mixed with conditioning agent, selective hydrogenation reaction is carried out in the presence of nickel-copper base catalyst, prepares cyclopentene;Wherein, the tune
Section agent is carbon monoxide.
2. according to the method described in claim 1, it is characterized in that, the molar ratio of the carbon monoxide and hydrogen is 1:(20-
100), preferably 1:(30-80), more preferably 1:(40-70).
3. method according to claim 1 or 2, which is characterized in that the nickel-copper base catalyst includes being supported on carrier
Nickel and copper, and optionally contain help active metal.
4. according to the method described in claim 3, it is characterized in that, it is described help active metal be selected from Li, Na, K, Cs, Ca, Mg,
It is one or more in Ba, La, Ce, Nd and Zn, it is preferably one or more in K, Mg, Ba and Cs.
5. method according to claim 3 or 4, which is characterized in that by the total weight of catalyst be 100% in terms of, it is described to help
The content of active metal is 0-3wt%, preferably 0-2.0wt%, more preferably 0.01-1.0wt%.
6. method according to any one of claims 1-5, which is characterized in that by the total weight of catalyst be 100% in terms of,
The content of nickel is 1-30wt%, preferably 3-25wt%, more preferably 4-20wt%;The content of copper is 0.1-8wt%.
7. according to the method described in any one of claim 1-6, which is characterized in that the liquid phase diluent is esters chemical combination
Object, preferably methyl formate, butyl formate, ethyl acetate, butyl acetate, isopropyl acetate, sec-butyl acetate, pentyl acetate,
One kind or more in isoamyl acetate, methyl amyl acetate, n-butyl propionate, isopropyl acetoacetate and ethyl acetoacetate
Kind, it is more preferably one or more in ethyl acetate, pentyl acetate and ethyl acetoacetate.
8. according to the described method of any one of claim 1-7, which is characterized in that the molar ratio of the hydrogen and cyclopentadiene
For (0.5-8):1, preferably (1-5):1, more preferably (1.2-3.0):1.
9. according to the method described in any one of claim 1-8, which is characterized in that the cyclopentadiene and liquid phase diluent
Weight ratio is 1:(5-10);Catalyst loading is 3-20h-1, preferably 5-15h-1。
10. according to the method described in any one of claim 1-9, which is characterized in that the temperature of the selective hydrogenation reaction is
0-150 DEG C, preferably 15-120 DEG C, more preferably 40-100 DEG C;Reaction pressure is 0.1-5.0MPa, preferably 0.5-
3.0MPa。
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110721681A (en) * | 2019-11-12 | 2020-01-24 | 西安凯立新材料股份有限公司 | Catalyst for preparing cyclopentene by cyclopentadiene hydrogenation, preparation method and application |
| CN114289024A (en) * | 2022-01-11 | 2022-04-08 | 万华化学集团股份有限公司 | Maleic anhydride hydrogenation catalyst and preparation method thereof |
| CN115888727A (en) * | 2022-11-28 | 2023-04-04 | 浙江卫星能源有限公司 | Nickel-based sulfur-resistant catalyst for selective hydrogenation of propyne to propylene, preparation method and application thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110721681A (en) * | 2019-11-12 | 2020-01-24 | 西安凯立新材料股份有限公司 | Catalyst for preparing cyclopentene by cyclopentadiene hydrogenation, preparation method and application |
| CN110721681B (en) * | 2019-11-12 | 2023-01-24 | 西安凯立新材料股份有限公司 | Catalyst for preparing cyclopentene by cyclopentadiene hydrogenation, preparation method and application |
| CN114289024A (en) * | 2022-01-11 | 2022-04-08 | 万华化学集团股份有限公司 | Maleic anhydride hydrogenation catalyst and preparation method thereof |
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| CN115888727A (en) * | 2022-11-28 | 2023-04-04 | 浙江卫星能源有限公司 | Nickel-based sulfur-resistant catalyst for selective hydrogenation of propyne to propylene, preparation method and application thereof |
| CN115888727B (en) * | 2022-11-28 | 2025-01-10 | 浙江卫星能源有限公司 | Nickel-based sulfur-resistant catalyst for synthesizing propylene by selective hydrogenation of propyne, preparation method and application thereof |
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