JP2010069384A - Olefin production catalyst and method of producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a high olefin selectivity catalyst capable of producing an olefin from an aldehyde which is easily made from am alcohol, and to provide an olefin production method using the catalyst. <P>SOLUTION: The olefin production catalyst includes a regularly mesoporous body and a metallic element supported thereon. The olefin production method comprises bringing an aldehyde which is easily made from an alcohol, into contact with the catalyst to form an olefin. Therefore, the olefin can be obtained in a high yield. Further, since the raw material is an aldehyde, this method can solve the problem as seen in the case where propylene is formed from ethanol in which ethylene is formed, and a further reaction is suppressed and an ethylene yield becomes high, and propylene can hardly be obtained. Furthermore, the method can also solve the problem as seen in the case where an acidic catalyst such as zeolite is used in which the catalyst life becomes shortened due to catalyst degeneration. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a catalyst for producing olefins using aldehyde as a raw material, and a method for producing olefins using the catalyst.

Production of lower olefins (ethylene, propylene, butene) is currently carried out by the pyrolysis method of petroleum fractions. However, there is a demand for a method for producing lower olefins from raw materials other than petroleum due to the problem of exhaustion of petroleum resources, etc., and a method for producing lower olefins using natural gas or alcohol synthesized from coal or dimethyl ether (hereinafter DME) Has been reported (see Patent Document 1). Furthermore, in recent years, a production method using bioalcohol, which is carbon neutral that does not use fossil raw materials, as a raw material has been reported (see Patent Document 2).
In the production of lower olefins from alcohols, zeolites that are acid catalysts are generally used as represented by MTO (Methanol To Olefin) reaction (see Patent Document 3). Furthermore, it has been proposed to use a zeolite catalyst in the reaction for producing propylene from bioethanol (see Patent Document 2).

JP 2007-290991 A JP 2007-291076 A JP-A-1-50827

However, while the acid catalyst is highly active, it has a problem that a wide range of products are generated and the selectivity of the target product is low, and deterioration such as carbon deposition and dealumination tends to proceed. In order to solve these problems, improvement methods such as controlling the pore diameter of the zeolite catalyst and controlling the acid strength by adding an additive have been studied. Is not a good solution.
In recent years, studies on the production of lower olefins from ethanol have been conducted in consideration of bioethanol. However, a zeolite catalyst is used in the same manner as described above, and a solution to the fundamental problem as an acid catalyst is not shown. In particular, when using an acid catalyst in the case of using ethanol, there is a problem that the dehydration reaction of ethanol proceeds, ethylene is generated, and further reaction is difficult to proceed.
In addition, there is a proposal of a mesoporous catalyst that supports metal as a new catalyst that does not use zeolite, but this catalyst may improve the problems of acid catalyst, but the ethanol reaction results show that the yield of ethylene There is a problem that becomes higher.

  An object of the present invention is to provide a catalyst having a high selectivity of olefins from aldehydes using aldehydes that can be easily produced from alcohol, and a method for producing olefins using the catalysts.

The present invention is an olefin production catalyst for producing an olefin having 3 or more carbon atoms from an aldehyde, wherein any one element from Group 6 elements of the Periodic Table to Group 13 elements of the Periodic Table is contained in the regular mesoporous material. An olefin production catalyst characterized by being supported.
As a result, the catalyst of the present invention can obtain a desired olefin in a high yield. In addition, since aldehyde is used as a raw material, it is possible to prevent a large amount of ethylene from being produced as in the case of producing propylene directly from ethanol, and it is possible to prevent further reaction from proceeding. Therefore, the fear that the yield of ethylene becomes high and it becomes difficult to obtain the desired propylene can be eliminated.

In the present invention, the element supported on the regular mesoporous material is at least one selected from iron, cobalt, nickel, aluminum, manganese, copper, zinc and chromium (hereinafter referred to as iron, cobalt, It may be abbreviated as nickel). More preferably, it is at least one selected from iron, cobalt, and nickel.
Thus, the catalyst of the present invention can obtain a desired olefin in a higher yield. In addition, since aldehyde is used as a raw material, it is possible to prevent a large amount of ethylene from being produced as in the case of producing propylene directly from ethanol, and it is possible to prevent further reaction from proceeding. Therefore, the fear that the yield of ethylene becomes high and it becomes difficult to obtain the desired propylene can be eliminated. Furthermore, the problem that the catalyst life is shortened due to catalyst deterioration, such as when an acidic catalyst such as a zeolite catalyst is used, can be solved.

In the present invention, the skeleton constituting the regular mesoporous material preferably has a structure in which the main component is silica.
In the present invention, the main component of the skeleton constituting the regular mesoporous material is silica.
As a result, iron, cobalt, nickel, and the like can be favorably supported, so that a regular mesoporous material having good physical properties can be obtained. Therefore, a catalyst having a high catalytic function can be obtained, and a desired olefin can be obtained in a higher yield.

In the present invention, it is preferable that the regular mesoporous material has an opening diameter of 1.4 nm or more and 10 nm or less.
In the present invention, a regular mesoporous material prepared with an opening diameter of 1.4 nm or more and 10 nm or less is used.
As a result, the desired olefin can be obtained in a higher yield.

In the present invention, the aldehyde is preferably at least one selected from acetaldehyde, paraaldehyde, crotonaldehyde, and butyraldehyde.
In the present invention, acetaldehyde, paraaldehyde, crotonaldehyde, and butyraldehyde are used as aldehydes.
As a result, the desired olefin can be obtained in a higher yield.

In the present invention, the aldehyde is preferably obtained by dehydrogenating alcohol, obtained by oxidation, or obtained by fermentation reaction of sugar.
In the present invention, an aldehyde obtained by dehydrogenating or oxidizing alcohol or fermenting sugar is used.
This makes it possible to easily obtain the raw material aldehyde from the alcohol.

The present invention is an olefin production method for producing an olefin from an aldehyde, wherein the aldehyde is contacted with the olefin production catalyst according to any one of claims 1 to 6. It is.
In this invention, an aldehyde is brought into contact with an olefin production catalyst to produce an olefin.
Thereby, a desired olefin can be obtained with a high yield.

In the present invention, after the step of producing aldehydes obtained by dehydrogenating or oxidizing alcohol or fermenting sugar, the aldehydes obtained in the step are brought into contact with the olefin production catalyst. This is an olefin production method.
As a result, the raw aldehyde can be easily obtained from the alcohol, and the desired olefin can be obtained in a high yield.

Hereinafter, an embodiment according to the method for producing olefin of the present invention will be described.
In addition, this embodiment demonstrates the structure which manufactures propylene from acetaldehyde as a raw material as an aldehyde.

(Composition of catalyst)
The catalyst used for the production of olefin in the present embodiment is a regular mesoporous material.
This regular mesoporous material is an inorganic or inorganic-organic composite solid material having regular nanopores. In addition, you may use for a catalyst the thing in which an alumina granular material etc. are mixed, for example.

The skeleton constituting the regular mesoporous material is preferably composed mainly of silica.
Here, the method for synthesizing the regular mesoporous material is not particularly limited. For example, a method of synthesizing a silica precursor as a raw material using a quaternary ammonium salt having a higher alkyl group having 8 or more carbon atoms as a template. Etc. can be exemplified.
And as a kind of silica precursor, for example, amorphous silica such as colloidal silica, silica gel, fumed silica, alkali silicate such as sodium silicate and potassium silicate, alkoxide such as tetramethyl orthosilicate, tetraethyl orthosilicate, They can be used alone or in combination.
The type of template is not particularly limited, but the general formula CH ₃ (CH ₂ ) _n N (CH ₃ ) ₃ .X (n is an integer of 7 to 21, X is a halogen ion or a hydroxide ion) A halogenated alkyltrimethylammonium cationic surfactant is preferred.
Specific examples include n-octyltrimethylammonium bromide, n-decyltrimethylammonium bromide, n-dodecyltrimethylammonium bromide, n-tetradecyltrimethylammonium bromide, n-octadecyltrimethylammonium bromide and the like.
In addition, regular nanopores can be easily formed, properties such as strength are good, and periodic table group 6 elements to periodic table group 13 elements, particularly iron, cobalt, nickel, aluminum, manganese Silica is preferably used because it is easy to stably support at least one of copper, zinc and chromium.

Furthermore, as the regular mesoporous material, it is preferable to use one having an opening diameter of 1.4 nm to 10 nm, for example.
Here, when the opening diameter of the regular mesoporous material is smaller than 1.4 nm, for example, the diffusibility of the reaction molecules and the generated molecules may be lowered, and the reaction efficiency may be lowered.
On the other hand, when the opening diameter of the regular mesoporous material is larger than 10 nm, for example, the effect of pores, that is, good support of active components such as iron, cobalt, and nickel becomes difficult, and high yield may not be obtained. is there.
Accordingly, it is preferable to set the opening diameter of the regular mesoporous material to 1.4 nm or more and 10 nm or less in terms of producing propylene with a high yield.

As the catalyst, a regular mesoporous material carrying one or more metals selected from the group consisting of iron, cobalt, nickel, aluminum, manganese, copper, zinc and chromium may be used.
Here, the method for supporting the metal on the regular mesoporous material is not particularly limited, and for example, an impregnation method, a vapor deposition method, a supported complex decomposition method, and the like can be used.
In particular, the template ion exchange method in which metal ions and template ions are exchanged in an aqueous solvent without firing and removing the template stored in the pores synthesized with the regular mesoporous material is easy to manufacture. preferable.
Further, template ion exchange can use a method in which a regular mesoporous material having a template occluded in pores is brought into contact with a metal inorganic acid salt or organic acid salt aqueous solution.
The amount of the metal (Me) supported on the regular mesoporous material is, for example, an atomic ratio Si / Me of 5 or more and 500 or less, particularly 15 or more, based on silica constituting the skeleton of the regular mesoporous material. It is preferable that it is 100 or less.
Here, when the atomic ratio Si / Me is smaller than 5, the ratio of Me increases, it becomes difficult to suppress the formation of metal oxide particles having low catalytic activity, and the catalytic activity may be lowered.
On the other hand, when the atomic ratio Si / Me is larger than 500, the ratio of Me is decreased, and sufficient support of the highly dispersed metal cannot be obtained, and the catalytic activity may be lowered.
Accordingly, the metal loading is preferably set so that the atomic ratio Si / Me is 5 or more and 500 or less, particularly 15 or more and 100 or less.
In addition, the regular mesoporous material on which a metal is supported by template ion exchange is preferably subjected to a heat treatment in an atmosphere in which oxygen exists in order to remove the remaining template by firing.
Here, for example, the temperature of the heat treatment is preferably 200 ° C. or higher and 800 ° C. or lower, and more preferably 300 ° C. or higher and 600 ° C. or lower.
And when the temperature of heat processing becomes lower than 200 degreeC, there exists a possibility that time may be required for baking of a template.
On the other hand, when the temperature of the heat treatment is higher than 800 ° C., the silica constituting the pore walls may be collapsed.
Thus, the temperature of the heat treatment of the regular mesoporous material carrying a metal is preferably set to 200 ° C. or higher and 800 ° C. or lower, preferably 300 ° C. or higher and 600 ° C. or lower.

(Olefin production method)
In the method for producing olefin of the present invention, an aldehyde raw material is brought into contact with the above-described catalyst to produce or produce an olefin.
Here, the olefin production apparatus is not particularly limited. For example, a fixed bed gas phase flow reaction apparatus which is a reactor filled with the above-described catalyst and having a catalyst layer inside and capable of flowing an aldehyde raw material is used. Can be used.
As the raw material aldehyde, acetaldehyde is used as a raw material for the purpose of producing propylene with high selectivity.
Moreover, as an aldehyde raw material, other aldehydes may be mixed and water may be mixed. Further, as the aldehyde raw material, it is directly supplied to a fixed bed type gas flow reactor or supplied after being appropriately diluted with an inert gas such as nitrogen, helium, argon, carbon dioxide, that is, an inert gas is mixed. Also good. Furthermore, it is good also as a raw material what used alcohol as a starting material, and passed the dehydrogenation catalyst and converted into the aldehyde.
The aldehyde used in this embodiment is preferably formaldehyde, acetaldehyde, paraaldehyde, propionaldehyde, acrolein, propiolaldehyde, butyraldehyde, crotonaldehyde, valeraldehyde, capronaldehyde, heptone aldehyde (hereinafter referred to as acetaldehyde, paraaldehyde). , Crotonaldehyde, butyraldehyde, etc. may be omitted). Furthermore, the aldehyde is more preferably acetaldehyde, paraaldehyde, crotonaldehyde, or butyraldehyde.
In addition, a step of contacting the obtained aldehyde with the olefin production catalyst described above is provided after the step of producing an aldehyde obtained by dehydrogenating or oxidizing alcohol or fermenting sugar. Also good. In this case, the desired olefin can be obtained in a higher yield than when the olefin is directly produced from the alcohol raw material.
Further, it is possible to save energy and labor for transporting aldebid produced from ethanol to an olefin production apparatus using the olefin production catalyst of the present invention at another location.

And as reaction temperature, it is preferable that they are 150 degreeC or more and 600 degrees C or less. Here, when the reaction temperature is lower than 150 ° C., sufficient catalytic activity cannot be obtained, the reaction rate is lowered, and the production efficiency of olefin may be lowered.
On the other hand, if the reaction rate is higher than 600 ° C., for example, coke may be generated, which may cause deterioration of catalytic activity.
Accordingly, the reaction temperature is preferably 150 ° C. or more and 500 ° C. or less, and more preferably set to 250 ° C. or more and 500 ° C. or less.
The reaction pressure of the raw material gas can be appropriately set within a wide range from normal pressure to high pressure. From the viewpoint of manufacturability and apparatus configuration, it is preferable to set the pressure from normal pressure to about 1.0 MPa.

The contact time between the aldehyde raw material and the catalyst is, for example, 0.001 (g-catalyst · second) / (mL-raw aldehyde gas) to 10 (g-catalyst · second) when the aldehyde raw material is reacted in the gas phase. / (ML-raw material aldehyde gas) or less, particularly 0.01 (g-catalyst · second) / (mL-raw material aldehyde gas) or more and 10 (g-catalyst · second) / (mL-raw material aldehyde gas) or less. Is preferred.
Here, when the contact time with the catalyst is shorter than 0.001 (g-catalyst · second) / (mL-raw aldehyde gas), the improvement of the conversion of the raw olefin cannot be expected, and the desired olefin is obtained at a high yield. It may become impossible to manufacture at a high rate.
On the other hand, if the contact time with the catalyst is longer than 10 (g-catalyst · second) / (mL-raw aldehyde gas), side reactions such as polymerization may occur, and the desired olefin may not be obtained in a high yield. There is.
Thus, the contact time between the raw aldehyde gas and the catalyst is 0.001 (g-catalyst · second) / (mL-raw aldehyde gas) or more and 10 (g-catalyst · second) / (mL-raw aldehyde gas). In the following, it is particularly preferable to set it to 0.01 (g-catalyst · second) / (mL-raw aldehyde gas) or more and 10 (g-catalyst · second) / (mL-raw aldehyde gas).

Moreover, when water is contained in the raw material aldehyde, the amount of water supplied in the raw material aldehyde is preferably 50 vol% or less.
Here, when the amount of water supply in the raw material aldehyde is more than 50 vol%, the conversion rate of the aldehyde is lowered, and there is a possibility that the olefin cannot be obtained in a high yield.
Thus, the water supply amount in the raw material aldehyde is preferably set to 50 vol% or less, preferably 40 vol% or less, more preferably 30 vol% or less.

(Effect of embodiment)
In the above-described embodiment, any one element among the 6th to 13th group elements is supported on the regular mesoporous material.
For this reason, a desired olefin can be obtained with a high yield. In addition, since aldehyde is used as a raw material, ethylene is produced as in the case of producing propylene from ethanol, and further reaction is unlikely to proceed, resulting in a high yield of ethylene and difficulty in obtaining desired propylene. Can be eliminated. Furthermore, the problem that the catalyst life is shortened due to catalyst deterioration, such as when an acidic catalyst such as a zeolite catalyst is used, can be solved.

In the above embodiment, the element supported on the regular mesoporous material is at least one selected from at least one of iron, cobalt, nickel, aluminum, manganese, copper, zinc, and chromium.
For this reason, a desired olefin can be obtained with a higher yield. In addition, since aldehyde is used as a raw material, ethylene is produced as in the case of producing propylene from ethanol, and further reaction is unlikely to proceed, resulting in a high yield of ethylene and difficulty in obtaining desired propylene. Can be eliminated.

In the above embodiment, the main component of the skeleton constituting the regular mesoporous material is silica.
For this reason, since iron, cobalt, nickel, etc. can be carry | supported favorably, the regular mesoporous body of a favorable physical property can be obtained. Therefore, a catalyst having a high catalytic function can be obtained, and a desired olefin can be obtained in a higher yield.

In the above embodiment, a regular mesoporous material having an opening diameter of 1.4 nm or more and 10 nm or less is used.
For this reason, a desired olefin can be obtained with a higher yield.

In the above embodiment, acetaldehyde, paraaldehyde, crotonaldehyde, butyraldehyde or the like is used as the aldehyde.
For this reason, a desired olefin can be obtained with a higher yield.

In the said embodiment, the aldehyde obtained by dehydrogenating or oxidizing alcohol or fermenting sugar is used.
For this reason, a desired olefin can be obtained with a higher yield by once converting it to an aldehyde even from an alcohol raw material.

In the above embodiment, the aldehyde is produced by contacting the aldehyde with the olefin production catalyst.
For this reason, a desired olefin can be easily obtained with a high yield by using an olefin production catalyst.

In the above-described embodiment, the olefin is obtained by contacting the obtained aldehyde with the olefin production catalyst described above after the step of producing an aldehyde obtained by dehydrogenating or oxidizing alcohol or fermenting sugar. The manufacturing method is disclosed.
For this reason, compared with the case where an olefin is directly manufactured from an alcohol raw material, a desired olefin can be obtained with a higher yield.

(Modification of the embodiment)
The aspect described above shows one aspect of the present invention, and the present invention is not limited to the above-described embodiment, and within the scope of achieving the objects and effects of the present invention. Needless to say, the modifications and improvements are included in the contents of the present invention.
In addition, the specific structure and shape in carrying out the present invention may be used as other structures and shapes within the scope of achieving the object and effect of the present invention.

That is, the production apparatus for carrying out the olefin production method of the present invention is not limited to the above-described fixed bed gas phase flow reaction apparatus. For example, any configuration in which the raw material is brought into contact with the catalyst, such as bringing the raw material gas into contact with the catalyst as a fluidized bed, can be applied.
Furthermore, as a catalyst, it can utilize with various forms, such as a granular material and a lump, what is called a honeycomb structure.
In addition, the catalyst is not limited to the silica mesoporous material, and any composition may be applied as long as it is a regular mesoporous material such as a material in which the main component of the skeleton includes other inorganic materials such as alumina. it can.
And as a catalyst, not only the structure which uses a regular mesoporous body by itself but as mentioned above, 1 type or 2 types chosen from the group of iron, cobalt, nickel, aluminum, manganese, copper, zinc, and chromium You may use what carried the above.

The physical properties of the ordered mesoporous material, and the physical properties of the catalyst such as one or more supported amounts selected from the group of iron, cobalt, nickel, etc. supported on the ordered mesoporous material are limited to the above-mentioned conditions. However, it can be appropriately set depending on the processing efficiency, the apparatus configuration, and the like.
Furthermore, the aldehyde raw material is not limited to acetaldehyde and the like as long as it corresponds to the product olefin, and may further contain water or other aldehydes.
Further, the reaction treatment conditions which are the contact conditions with the catalyst of the raw material aldehyde gas obtained by vaporizing the aldehyde raw material are not limited to the above-mentioned conditions. It can be set appropriately depending on the device configuration.

In addition, the specific structure and shape in the implementation of the present invention may be other structures as long as the object of the present invention can be achieved.
[Example]

  Next, the manufacturing method of the olefin of this invention is demonstrated concretely by an Example. The present invention is not limited to the following examples.

(Preparation of catalyst)
Snowtex 20 (colloidal silica) manufactured by Nissan Chemical Industries, Ltd. was used as the silica source, and dodecyltrimethylammonium bromide (manufactured by Tokyo Chemical Industry) as the surfactant. All experimental tools were made of tetrafluoroethylene.
First, 641.4 g of ion-exchanged water was mixed with 225.0 g of a surfactant and stirred vigorously. Snowtex 20 (306.7 g) and aqueous sodium hydroxide solution (NaOH 11.7 g + H ₂ O 125.6 g) were alternately added dropwise thereto.
And after dripping all, the mixed solution was stirred at 313K for 2 hours. At this time, the final pH of the mixed solution was 11.6.
This mixed solution was hydrothermally treated at 413 K in an autoclave for 48 hours under standing conditions. The obtained white product was filtered and washed with 2 L of ion exchange water, and then dried overnight at 353 K in a dryer.
3.0 g of the dried sample was added to 30 mL of ion-exchanged water and stirred to make it suspend. An aqueous solution prepared by dissolving 0.38 g of nickel nitrate hexahydrate (special grade reagent manufactured by Wako Pure Chemical Industries, Ltd.) in 30 mL of ion exchange water was slowly added dropwise thereto. After completion of the addition, stirring was continued for 1 hour at room temperature. After stirring, the mixture was allowed to stand in a 353 K water bath for 20 hours. Thereafter, the mixture was filtered, dispersed in about 1 L of ion exchange water, stirred for 5 minutes, filtered, and dried overnight at 353K. The dried sample was spread thinly on a magnetic dish, heated to 773 K, and baked for 6 hours to obtain Ni-M41. The Si / Ni atomic ratio of this Ni-M41 was 21.3.

(Reaction of acetaldehyde)
Acetaldehyde was reacted using Ni-M41 as a catalyst. 100 mg of catalyst is packed in the center of a SUS reaction tube having an inner diameter of 5 mm. Prior to the reaction, as a pretreatment of the catalyst, the temperature was raised to 673 K over 40 minutes while flowing 100 mL / min of nitrogen gas and held at 673 K for 1 hour. Thereafter, 0.5 μL of a target raw material (acetaldehyde, ethanol, etc.) was injected into this nitrogen stream and reacted through the catalyst layer.
About the analysis of the product, it analyzed by the FID gas chromatography directly connected with the reaction tube.
In Comparative Examples 2 and 3, the reaction was carried out using a commercially available zeolite catalyst H-ZSM-5 instead of Ni-M41.
The obtained results are shown in Table 1.

(result)
The results of component analysis of the products of Comparative Examples 1 to 3 and Examples 1 to 4 are shown below.
[Comparative Example 1]

In Comparative Example 1, ethanol was reacted with a metal-supported mesoporous material catalyst (Ni-M41). In this case, although high ethanol conversion was shown, the main product was ethane and the yield of propylene was low.
[Comparative Example 2]

In Comparative Example 2, ethanol was reacted with H-ZSM-5, which is a zeolite catalyst. In this case, high ethanol conversion was shown, but the propylene yield in the product was lower than the ethylene yield.
[Comparative Example 3]

  In Comparative Example 3, acetaldehyde was reacted with H-ZSM-5 which is a zeolite catalyst. In this case, the ethylene yield and the propylene yield are comparable, but the olefin yield is generally low. From this, it was confirmed that the use of zeolite as an acid catalyst for olefin production using aldehyde as a raw material has no effect.

  In Example 1, acetaldehyde was reacted with a metal-supported mesoporous material catalyst (Ni-M41). In this case, the ethylene yield was greatly suppressed as compared with Comparative Example 1, and the propylene yield increased. This made propylene the main product in the olefin.

  In Example 2, crotonaldehyde was reacted with a metal-supported mesoporous material catalyst (Ni-M41). In this case, compared with Comparative Example 1 and Example 2, the ethylene yield was further suppressed and the propylene yield increased. Among Comparative Examples 1 to 3 and Examples 1 to 4, the propylene / ethylene ratio was maximized.

  In Example 3, butyraldehyde was reacted with a metal-supported mesoporous material catalyst (Ni-M41). In this case, as in Examples 1 and 2, the ethylene yield was greatly suppressed, and the propylene yield increased. In addition, the yield of olefins other than propylene was high.

  In Example 4, a dehydrogenation catalyst (G-99C manufactured by Zude Chemie Catalysts Co., Ltd.) was charged in the previous stage of the mesoporous catalyst (Ni-M41) supporting a metal, and ethanol was reacted. In this case, the ethylene yield was greatly suppressed as compared with Comparative Example 1, and the propylene yield increased. Thereby, in Comparative Examples 1-3 and Examples 1-4, the propylene yield became the maximum.

(Summary)
From the above, when producing propylene from an aldehyde, a high propylene yield cannot be realized even if a zeolite catalyst which is an acid catalyst is used. However, a high propylene yield can be realized by using a mesoporous catalyst (Ni-M41) carrying a metal.
Moreover, when producing propylene using ethanol as a raw material, the propylene yield is increased by first converting ethanol to acetaldehyde by a dehydrogenation reaction.
Furthermore, it can apply also about aldehydes other than acetaldehyde as an aldehyde. For example, even when crotonaldehyde is used, a high propylene yield can be obtained.

The present invention can be used in a method for producing an olefin using an aldehyde as a raw material.

Claims (9)

An olefin production catalyst for producing an olefin having 3 or more carbon atoms from an aldehyde,
An olefin production catalyst characterized in that an ordered mesoporous material is loaded with any one element from Group 6 elements of the Periodic Table to Group 13 elements of the Periodic Table. The olefin production catalyst according to claim 1,
The element supported on the regular mesoporous material is at least one selected from iron, cobalt, nickel, aluminum, manganese, copper, zinc and chromium. The olefin production catalyst according to claim 1 or 2,
The skeleton that constitutes the ordered mesoporous material has a main component of silica as a olefin production catalyst. The olefin production catalyst according to any one of claims 1 to 3,
An opening diameter of the regular mesoporous material is 1.4 nm or more and 10 nm or less. The olefin production catalyst according to any one of claims 1 to 4,
The aldehyde is an olefin production catalyst characterized by being at least one selected from acetaldehyde, paraaldehyde, crotonaldehyde, and butyraldehyde. An olefin production catalyst according to any one of claims 1 to 5,
The aldehyde is obtained by dehydrogenating alcohol, obtained by oxidation, or obtained by fermentation reaction of sugar. An olefin production method for producing an olefin from an aldehyde,
The said aldehyde is made to contact the olefin production catalyst as described in any one of Claims 1-6. The olefin production method characterized by the above-mentioned. The olefin production method according to claim 7,
As the aldehyde, an aldehyde obtained by dehydrogenating alcohol, an aldehyde obtained by oxidation, or an aldehyde obtained by fermentation reaction of sugar is used.   The aldehyde obtained by the said process is used as described in any one of Claims 1-6 after the process of dehydrogenating or oxidizing alcohol, or manufacturing the aldehyde obtained by fermenting sugar. An olefin production method comprising contacting with the olefin production catalyst described in 1.