JP2003053193A - Oxidation catalyst and carbonyl compound using the same and method of manufacturing hydrogen peroxide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an oxidation catalyst which is capable of efficiently oxidizing an alcohol and an oxidation method. SOLUTION: The oxidation catalyst consisting of the imide compound expressed by the following formula (1) Formula (1) [wherein R<1> and R<2> may be the same or different and denote hydrogen atoms, halogen atoms, alkyl groups, etc.; R<1> and R<2> may form double bonds or rings, etc., by bonding to each other; X denotes an oxygen atom or hydroxyl group and the N-substituted cyclic imide group, shown in the formula (1) described above, may be further formed in one or two pieces in the double bonds or the rings, formed by bonding R<1> or R<2> or R<1> and R<2> to each other and titanium dioxide is provided. The titanium oxide preferably contains at least a rutile type titanium dioxide. The oxidation method of oxidizing a primary or secondary alcohol in the presence of the oxidation catalyst described above is provided.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an oxidation catalyst useful for efficiently oxidizing an alcohol, a method for oxidizing an alcohol using the oxidation catalyst, and a method for producing a carbonyl compound and hydrogen peroxide.

[0002]

2. Description of the Related Art It is known that a peroxide is produced by autoxidation of an organic substrate, but the reaction rate is very small under mild conditions. Generally, metal catalysts are used to improve the rate of autoxidation, but these metal catalysts also accelerate the decomposition of peroxide. Therefore, it becomes difficult to retain the generated peroxide in the reaction system, and the peroxide cannot be obtained in good yield.

On the other hand, WO 00/46145 discloses a method for producing hydrogen peroxide by reacting a primary or secondary alcohol with oxygen using an imide compound as a catalyst. This document also describes that the reaction produces an aldehyde or ketone corresponding to the substrate. However, the above method has a low reaction rate and requires a long reaction time.

[0004]

SUMMARY OF THE INVENTION Therefore, an object of the present invention is to provide an oxidation catalyst and an oxidation method capable of efficiently oxidizing an alcohol. Another object of the present invention is to
It is intended to provide a method for efficiently producing a corresponding carbonyl compound and / or hydrogen peroxide from a secondary or secondary alcohol.

[0005]

Means for Solving the Problems As a result of intensive investigations by the present inventors in order to achieve the above object, the use of an oxidation catalyst in which an imide compound having a specific structure and titanium dioxide are combined accelerates the oxidation reaction. At the same time, it was found that the decomposition of the generated hydrogen peroxide can be remarkably suppressed and can be stably retained in the system, and the present invention has been completed.

That is, the present invention provides the following formula (1):

[Chemical 2] [Wherein R ¹ and R ² are the same or different and each represents a hydrogen atom,
Represents a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, an acyl group, R ¹ and R ² are bonded to each other to form a double bond, or an aromatic group or It may form a non-aromatic ring. X represents an oxygen atom or a hydroxyl group. Said R ¹ , R ² , or R ¹ and R ²
A double bond or an aromatic or non-aromatic ring formed by being bonded to each other has N represented by the above formula (1).
-The substituted imide group may further have 1 or 2 formed.] And an oxidation catalyst comprising titanium dioxide. In this oxidation catalyst, for example, titanium dioxide containing at least rutile titanium dioxide is used as titanium dioxide.

The present invention also provides an oxidation method for oxidizing a primary or secondary alcohol with oxygen in the presence of the above-mentioned oxidation catalyst.

The present invention is further characterized by reacting a primary or secondary alcohol with oxygen in the presence of the above-mentioned oxidation catalyst to obtain a corresponding carbonyl compound and / or hydrogen peroxide. A method for producing a carbonyl compound and / or hydrogen peroxide is provided.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The oxidation catalyst of the present invention comprises an imide compound as a main catalyst and titanium dioxide as a co-catalyst. [Imide Compound] In the present invention, the catalyst represented by the above formula (1) is used.
An imide compound represented by In equation (1),
Among the substituents R ¹ and R ² , the halogen atom includes iodine, bromine, chlorine and fluorine. Alkyl groups include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl,
A linear or branched alkyl group having about 1 to 10 carbon atoms such as hexyl, heptyl, octyl and decyl groups is included. Preferred alkyl groups include, for example, 1 to 1 carbon atoms.
Examples thereof include lower alkyl groups having about 6 carbon atoms, particularly about 1 to 4 carbon atoms.

Aryl groups include phenyl and naphthyl groups, and cycloalkyl groups include cyclopentyl and
A cyclohexyl group and the like are included. Alkoxy groups include
For example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, t-butoxy, pentyloxy, hexyloxy groups and the like have about 1 to 10 carbon atoms, preferably about 1 to 6 carbon atoms, and particularly about 1 to 4 carbon atoms. And lower alkoxy groups of

The alkoxycarbonyl group includes, for example, a carbon of an alkoxy moiety such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, t-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl group. The number of alkoxycarbonyl groups is about 1 to 10. Preferred alkoxycarbonyl groups include lower alkoxycarbonyl groups having an alkoxy moiety with about 1 to 6 carbon atoms, particularly about 1 to 4 carbon atoms.

As the acyl group, for example, formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl groups and the like having 1 to 6 carbon atoms can be mentioned.
A degree of acyl group can be exemplified.

The substituents R ¹ and R ² may be the same or different. In the above formula (1), R ¹ and R ² may be bonded to each other to form a double bond or a ring having an aromatic or non-aromatic attribute. The preferred aromatic or non-aromatic ring is a 5- to 12-membered ring, especially a 6- to 10-membered ring, which may be a heterocyclic ring or a condensed heterocyclic ring, but is often a hydrocarbon ring. Such rings include, for example:
Non-aromatic alicyclic ring (such as cycloalkane ring which may have a substituent such as cyclohexane ring and cycloalkene ring which may have a substituent such as cyclohexene ring), non-aromatic bridge Bridged ring (such as bridged hydrocarbon ring which may have a substituent such as 5-norbornene ring),
Included are aromatic rings (including condensed rings) that may have a substituent such as a benzene ring and a naphthalene ring. The ring is
Often composed of aromatic rings. The ring may have a substituent such as an alkyl group, a haloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, an acyl group, a nitro group, a cyano group, an amino group and a halogen atom.

In the above general formula (1), X represents an oxygen atom or a hydroxyl group, and the bond between the nitrogen atom N and X is a single bond or a double bond.

The double bond or aromatic or non-aromatic ring formed by combining R ¹ , R ² , or R ¹ and R ² with each other is represented by the above formula (1). One or two N-substituted cyclic imide groups may be further formed. For example, when R ¹ or R ² is an alkyl group having 2 or more carbon atoms, the N-substituted cyclic imide group may be formed by including two adjacent carbon atoms forming the alkyl group. When R ¹ and R ² are bonded to each other to form a double bond, the N-substituted cyclic imide group may be formed by including the double bond. Further, when R ¹ and R ² are bonded to each other to form an aromatic or non-aromatic ring, the N-substituted cyclic imide group is formed by including two adjacent carbon atoms constituting the ring. It may have been done.

Preferred imide compounds include compounds represented by the following formula.

[Chemical 3] (In the formula, R ^{3 to} R ⁶ are the same or different and are a hydrogen atom, an alkyl group, a haloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, an acyl group, a nitro group, a cyano group, an amino group, In R ^{3 to} R ⁶ , adjacent groups may be bonded to each other to form an aromatic or non-aromatic ring, and in the formula (1f), A is a methylene group or Represents an oxygen atom, R ¹ ,
R ² and X are the same as above. The benzene ring of formula (1c) may further have 1 or 2 N-substituted cyclic imide groups represented by formula (1c).

In the substituents R ^{3 to} R ⁶ , the alkyl group includes the same alkyl groups as those exemplified above, particularly an alkyl group having about 1 to 6 carbon atoms, and the haloalkyl group includes trifluoromethyl. The haloalkyl group having about 1 to 4 carbon atoms such as a group and the alkoxy group have the same alkoxy group as described above, particularly a lower alkoxy group having about 1 to 4 carbon atoms,
The alkoxycarbonyl group includes the same alkoxycarbonyl group as described above, particularly a lower alkoxycarbonyl group having an alkoxy moiety having about 1 to 4 carbon atoms. As the acyl group, the same acyl group as described above, particularly 1 carbon atom
Examples of the acyl group include about 6 to 6, and examples of the halogen atom include fluorine, chlorine and bromine atoms. Substituent R ³
In most cases, R ⁶ to R ⁶ are usually a hydrogen atom, a lower alkyl group having about 1 to 4 carbon atoms, a carboxyl group, a nitro group, or a halogen atom. The ring formed by R ^{3 to} R ⁶ bonded to each other is the same as the ring formed from R ¹ and R ² bonded to each other, and particularly aromatic or non-aromatic 5 to 12
Member rings are preferred.

As typical examples of preferable imide compounds, for example, N-hydroxysuccinimide, N-hydroxymaleic acid imide, N-hydroxyhexahydrophthalic acid imide, N, N'-dihydroxycyclohexanetetracarboxylic acid imide, N-hydroxyphthalic acid imide, N-hydroxytetrabromophthalic acid imide, N
-Hydroxytetrachlorophthalimide, N-hydroxyhetimide, N-hydroxyhymic acid imide, N-hydroxytrimellitic imide, N, N'-
Examples thereof include dihydroxypyromellitic imide and N, N′-dihydroxynaphthalene tetracarboxylic imide.

The imide compound represented by the formula (1) is subjected to a conventional imidation reaction, for example, by reacting a corresponding acid anhydride with hydroxylamine NH ₂ OH to undergo ring opening and ring closure of an acid anhydride group. It can be prepared by a method of imidization.

Examples of the acid anhydrides include saturated or unsaturated aliphatic dicarboxylic acid anhydrides such as succinic anhydride and maleic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride (1,2-cyclohexanedicarboxylic acid anhydride). Products), saturated or unsaturated non-aromatic cyclic polyvalent carboxylic acid anhydrides such as 1,2,3,4-cyclohexanetetracarboxylic acid 1,2-anhydride (alicyclic polyvalent carboxylic acid anhydrides), Bridged cyclic polyvalent carboxylic acid anhydride (alicyclic polyvalent carboxylic acid anhydride) such as het anhydride, hymic acid anhydride, phthalic anhydride, tetrabromophthalic anhydride, tetrachlorophthalic anhydride, nitrophthalic anhydride, Trimellitic anhydride, methylcyclohexene tricarboxylic anhydride, pyromellitic anhydride, mellitic anhydride, 2, 3; 6,
Included are aromatic polyhydric carboxylic acid anhydrides such as 7-naphthalene tetracarboxylic dianhydride.

Particularly preferred imide compounds are alicyclic polyvalent carboxylic acid anhydrides or aromatic polyvalent carboxylic acid anhydrides, especially N-derived from aromatic polyvalent carboxylic acid anhydrides.
Hydroxyimide compounds such as N-hydroxyphthalic acid imide are included.

The imide compound represented by the formula (1) may be used alone or in combination of two or more. The imide compound may be used in the form of being supported on a carrier. As the carrier, a porous carrier such as activated carbon, zeolite, silica, silica-alumina or bentonite is often used.

The amount of the imide compound used can be selected within a wide range, for example, 0.00000 per mol of the substrate.
1 to 1 mol, preferably 0.00001 to 0.5 mol,
More preferably, it is about 0.001 to 0.4 mol,
It is often 0.01 to 0.35 mol.

[Titanium Dioxide] The titanium dioxide used as a catalyst in the present invention may have any crystal structure such as rutile type and anatase type, and is a mixture of plural kinds of titanium dioxide having different crystal structures. May be The mixture is not only a mixture of a plurality of types of titanium dioxide having different crystal structures (a mixture of rutile type and anatase type titanium dioxide),
After mixing, one titanium dioxide (for example, anatase type titanium dioxide) particles is carried on the surface of the other titanium dioxide (for example, rutile type titanium dioxide) particles by ultrasonic treatment or the like, or a dioxide having a single crystal structure. Examples include titanium (for example, anatase-type titanium dioxide) which has been converted into a mixture of titanium dioxide having a crystal structure of a plurality of types (for example, anatase-type titanium dioxide and rutile-type titanium dioxide) by heat treatment.

As titanium dioxide, in particular, titanium dioxide containing at least rutile titanium dioxide, such as rutile titanium dioxide or a mixture of rutile titanium dioxide and anatase titanium dioxide (for example, the content of rutile titanium dioxide is 5). % Or more, preferably 10% or more, of titanium dioxide) is preferably used.

The form of titanium dioxide is not particularly limited, and it may be in the form of powder (particles), lumps, films, or the like.
When using powdered titanium dioxide, the average particle size is
For example, about 0.005 to 100 μm, preferably 0.0
It is about 1 to 10 μm.

The amount of titanium dioxide used is the imide compound 1
The amount is, for example, 0.01 to 10 mol, preferably 0.1 to 5 mol, and more preferably 0.5 to 3 mol with respect to the mol.

[Oxidation Method] In the oxidation method of the present invention, the primary or secondary alcohol (substrate) is oxidized with oxygen in the presence of the oxidation catalyst. The primary or secondary alcohol includes a wide range of alcohols. Alcohol is 1
It may be either a dihydric or polyhydric alcohol. In addition, the primary or secondary alcohol includes various substituents such as a halogen atom, an oxo group, a hydroxyl group, a mercapto group, a substituted oxy group (for example, an alkoxy group, an aryloxy group, an acyloxy group, etc.) and a substituted group. Thio group, carboxyl group, substituted oxycarbonyl group, substituted or unsubstituted carbamoyl group, cyano group, nitro group, substituted or unsubstituted amino group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkenyl group, aryl group (Eg, phenyl, naphthyl group, etc.), aralkyl group, heterocyclic group, etc. may be contained.

As the primary alcohol, methanol,
Ethanol, 1-propanol, 1-butanol, 2-
Methyl-1-propanol, 1-pentanol, 1-hexanol, 1-octanol, 1-decanol, 1-
Hexadecanol etc. has 1 to 30 carbon atoms (preferably 1
~ 20, more preferably 1 to 15) saturated or unsaturated aliphatic primary alcohols; saturated or unsaturated alicyclic primary alcohols such as cyclopentylmethyl alcohol, cyclohexylmethyl alcohol, 2-cyclohexylethyl alcohol; Aromatic primary alcohols such as benzyl alcohol, 2-phenylethyl alcohol and 3-phenylpropyl alcohol; and heterocyclic alcohols such as 2-hydroxymethylpyridine. Preferred primary alcohols include aliphatic primary alcohols (for example, saturated aliphatic primary alcohols having about 1 to 20 carbon atoms) and the like.

As the secondary alcohol, 2-propanol, s-butyl alcohol, 2-pentanol, 3-
Pentanol, 2-hexanol, 2-octanol,
Carbon number 3 such as 4-decanol and 2-hexadecanol
-30 (preferably 3-20, more preferably 3-1)
5) about saturated or unsaturated aliphatic secondary alcohol; 3 to 20 members (preferably 3 to 20 members) such as cyclobutanol, cyclopentanol, cyclohexanol, cyclooctanol, cyclododecanol, cyclopentadecanol
15 members, more preferably 5 to 15 members, especially 5 to 8 members)
Saturated or unsaturated alicyclic secondary alcohols; aromatic secondary alcohols such as 1-phenylethanol, 2-phenylethanol, 1-phenylpropanol, 1-phenylmethylethanol, benzhydrol (diphenylmethanol) A heterocyclic secondary alcohol such as 1- (2-pyridyl) ethanol and the like are included.

Preferred substrates include secondary alcohols (eg, s-butyl alcohol, aliphatic secondary alcohols such as 2-octanol, alicyclic secondary alcohols such as cyclohexanol, 1-phenylethanol, 2 −
Aromatic secondary alcohols such as phenylethanol and benzhydrol) are included. The alcohols may be used alone or in admixture of two or more.

The oxygen may be either molecular oxygen or nascent oxygen. As the molecular oxygen, pure oxygen may be used, or oxygen diluted with an inert gas such as nitrogen, helium, argon or carbon dioxide may be used. From the viewpoint of not only operability and safety but also economy, it is preferable to use air.

The amount of oxygen used can be appropriately selected according to the kind of the substrate, but is usually 0.5 mol or more (for example, 1 mol or more), preferably 1 to 100 mol, and further 1 mol of the substrate. It is preferably about 2 to 50 mol. Often, an excess of oxygen is used with respect to the substrate.

[Reaction] The reaction is usually carried out in an organic solvent. Examples of the organic solvent include organic acids such as acetic acid and propionic acid; nitriles such as acetonitrile, propionitrile and benzonitrile; amides such as formamide, acetamide, dimethylformamide (DMF) and dimethylacetamide; hexane and octane. Aliphatic hydrocarbons; halogenated hydrocarbons such as chloroform, dichloromethane, dichloroethane, carbon tetrachloride, chlorobenzene and trifluoromethylbenzene; nitro compounds such as nitrobenzene, nitromethane and nitroethane; esters such as ethyl acetate and butyl acetate; And a mixed solvent thereof. As the solvent, organic acids such as acetic acid, nitriles such as acetonitrile and benzonitrile, halogenated hydrocarbons such as trifluoromethylbenzene, and esters such as ethyl acetate are often used.

The concentration of the substrate is, for example, 0.1 to 10 mol /
1, preferably 0.5 to 5 mol / l, more preferably 0.7 to 3 mol / l. If the concentration of the substrate is high, the selectivity of hydrogen peroxide is likely to decrease, and conversely, if the concentration of the substrate is low, it is economically disadvantageous.

The reaction temperature can be appropriately selected depending on the type of substrate, and is, for example, 0 to 200 ° C., preferably 30 to
The reaction temperature is 150 ° C, more preferably 40 to 120 ° C, and usually the reaction is usually performed at 50 to 100 ° C.
When the reaction is carried out at a temperature of 200 ° C. or higher, the decomposition of the produced hydrogen peroxide is promoted, so that the hydrogen peroxide cannot be retained in the system and the yield is lowered.

The reaction can be carried out under normal pressure or under pressure. When the reaction is performed under pressure, it is usually 0.1-10.
MPa (for example, 0.15 to 8 MPa), preferably about 0.2 to 7 MPa. The reaction time can be appropriately selected from the range of, for example, 30 minutes to 24 hours, preferably 1 to 20 hours, more preferably 2 to 15 hours, depending on the reaction temperature and pressure. The reaction can be carried out in the presence of oxygen or under the flow of oxygen by a conventional method such as a batch system, a semi-batch system or a continuous system.

In the method of the present invention, depending on the type of substrate, aldehyde (when the substrate is a primary alcohol) or ketone (when the substrate is a secondary alcohol) is used depending on the type of substrate.
And / or hydrogen peroxide is produced. In particular, using the oxidation catalyst of the present invention, without promoting the decomposition of hydrogen peroxide seen in the oxidation reaction using a metal catalyst such as cobalt,
Since the produced hydrogen peroxide can be retained in the reaction system, the hydrogen peroxide can be recovered in good yield.

After completion of the reaction, the reaction product (aldehyde or ketone and / or hydrogen peroxide) can be filtered, for example.
Separation and purification can be performed by a separation means such as concentration, distillation, extraction, crystallization, recrystallization, column chromatography, or a combination of these. Titanium dioxide can be easily recovered by filtration after the reaction. The generated aldehyde or ketone can be used for each purpose, or may be converted into a primary or secondary alcohol by a conventional reduction method and reused as a substrate. Further, the produced hydrogen peroxide can be used as an oxidizing agent for an organic substrate by being isolated from the system, or can be used as an oxidizing agent without isolation.

[0040]

According to the oxidation catalyst and the oxidation method of the present invention, alcohol can be efficiently oxidized. Further, according to the production method of the present invention, the oxidation reaction for producing the corresponding carbonyl compound and / or hydrogen peroxide from the primary alcohol or secondary alcohol and oxygen is promoted, and the produced hydrogen peroxide is The decomposition can be significantly suppressed,
It can be stably maintained in the system.

[0041]

The present invention will be described in more detail based on the following examples, but the invention is not intended to be limited by these examples. The amount of hydrogen peroxide produced was determined by adding 5 parts by weight of water and 2 parts by weight of ethylbenzene to 1 part by weight of the reaction solution for extraction, and subjecting the aqueous layer to an iodometric titration method.

Example 1 Benzhydrol 0.921 g (5 mmol), N-hydroxyphthalimide 0.082 g (0.5 mmol), rutile titanium dioxide powder [trade name "NS5
1 ", rutile type (rutile type content 98.6%); manufactured by Toho Titanium Co., Ltd.] 0.050 g (0.625 mmol), and 5 ml of acetonitrile in an oxygen atmosphere (1 atm = 0.1 MPa). The mixture was stirred at 75 ° C for 6 hours. When the reaction solution was analyzed by an iodometric titration method, hydrogen peroxide was produced in a yield of 23% (selectivity 56%).
When the composition of the reaction solution was examined by gas chromatography analysis, the conversion rate of benzhydrol was 40%, and benzophenone was produced at a yield of 30% (selectivity 73%).

Example 2 The same operation as in Example 1 was carried out except that as the titanium dioxide powder, trade name “ST-01” [anatase type (anatase type content 100%%); Ishihara Sangyo Co., Ltd.] was used. As a result, the conversion of benzhydrol was 18%, hydrogen peroxide was produced in a yield of 0%, and benzophenone was produced in a yield of 15% (selectivity: 83%).

Example 3 As titanium dioxide powder, titanium dioxide powder [rutile type (trade name "NS51" (rutile type content 98.6%); manufactured by Toho Titanium Co., Ltd.) 35 mg) and anatase type (trade name) "ST-01" (Anatase type content 100
%); Manufactured by Ishihara Sangyo Co., Ltd.) was carried out in the same manner as in Example 1 except that 15 mg was mixed by ultrasonic treatment. The conversion rate of benzhydrol was 55%, and hydrogen peroxide was The yield was 18% (selectivity: 33%) and benzophenone was produced in a yield of 34% (selectivity: 61%).

Comparative Example 1 The same operation as in Example 1 was carried out except that titanium dioxide was not used, and the conversion of benzhydrol was 8%.
And hydrogen peroxide yield 0% and benzophenone yield 8
% (Selectivity 99%).

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Claims (4)

[Claims] 1. The following formula (1): [Wherein R ¹ and R ² are the same or different and each represents a hydrogen atom,
It represents a halogen atom, an alkyl group, an aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group, an acyl group, and R ¹ and R ² are bonded to each other to form a double bond or an aromatic or non-aromatic group. It may form an aromatic ring. X represents an oxygen atom or a hydroxyl group. The double bond formed by R ¹ , R ² , or R ¹ and R ² bonded to each other or the aromatic or non-aromatic ring has N-type represented by the above formula (1).
1 or 2 substituted cyclic imide groups may be further formed], and an oxidation catalyst comprising titanium dioxide. 2. The oxidation catalyst according to claim 1, wherein the titanium dioxide contains at least rutile titanium dioxide. 3. In the presence of the oxidation catalyst according to claim 1,
Oxidation method of oxidizing a secondary or secondary alcohol with oxygen. 4. A first catalyst in the presence of the oxidation catalyst according to claim 1.
A method for producing a carbonyl compound and / or hydrogen peroxide, which comprises reacting a secondary or secondary alcohol with oxygen to obtain a corresponding carbonyl compound and / or hydrogen peroxide.