Method for producing aliphatic aldehydes

Abstract

This invention provides a method for producing aliphatic aldehydes in high yield by oxidizing aliphatic primary alcohols having four or more carbon atoms. [Solution] A method for producing an aliphatic aldehyde, comprising the step of oxidizing an aliphatic primary alcohol having 4 or more carbon atoms with molecular oxygen in the presence of an N-oxyl compound and / or an N-oxide compound and a metal-supported catalyst, The metal-supported catalyst includes a metal supported on an inorganic support, A method for producing an aliphatic aldehyde, wherein the N-oxyl compound and / or N-oxide compound is one or more selected from the group consisting of compounds represented by general formula (I), compounds represented by general formula (II), and compounds represented by general formula (III). [Formula 1] JPEG2026104778000025.jpg37124

Claims

1. A method for producing an aliphatic aldehyde, comprising the step of oxidizing an aliphatic primary alcohol having 4 or more carbon atoms with molecular oxygen in the presence of an N-oxyl compound and / or an N-oxide compound and a metal-supported catalyst, The metal-supported catalyst includes a metal supported on an inorganic support, A method for producing an aliphatic aldehyde, wherein the N-oxyl compound and / or N-oxide compound is one or more selected from the group consisting of compounds represented by general formula (I), compounds represented by general formula (II), and compounds represented by general formula (III). 【Chemistry 13】 [In the formula, R 1 , R 2 , R 3 , and R 4 R is a hydrocarbon group having 1 to 5 carbon atoms, which may be substituted with a hydrogen atom or a substituent, and the substituent is one or more selected from the group consisting of a halogen atom, a nitro group, an alkoxy group, a phenoxy group and an acyloxy group, 5 [This is an oxygen atom or a methylene group.] 【Chemistry 14】 [In the formula, R 11 、R 12 、R 13 、and R 14 are, independently of one another, a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may be substituted with a substituent, and the substituent is one or more selected from the group consisting of a halogen atom, a nitro group, an alkoxy group, a phenoxy group, and an acyloxy group. R 15 [This is an oxygen atom or a methylene group.] 【Chemistry 15】 [In the formula, R 6 , and R 7 These are, independently of each other, a hydrogen atom, an unsubstituted hydrocarbon group having 1 to 5 carbon atoms, or a hydrocarbon group having 1 to 5 carbon atoms that may be substituted with a substituent, and the substituent is one or more selected from the group consisting of a halogen atom, a nitro group, an alkoxy group, a phenoxy group, and an acyloxy group.

2. The manufacturing method according to claim 1, wherein the metal includes ruthenium.

3. The surface area per unit mass of the ruthenium metal is 60 m². 2 The manufacturing method according to claim 1, wherein the amount is 1 / g or more.

4. The manufacturing method according to claim 1, wherein the inorganic support comprises a porous oxide, one or more selected from the group consisting of alumina, titania, zirconia, silica, silicaalumina, magnesia, zeolite, and activated carbon.

5. The method for producing a product according to claim 1, wherein the aliphatic primary alcohol is an aliphatic linear saturated primary alcohol.

6. The manufacturing method according to claim 1, wherein the total molar ratio of the N-oxyl compound and the N-oxide compound to the metal is 0.01 or more and 20 or less.

7. The manufacturing method according to claim 1, wherein the total molar ratio of the N-oxyl compound and the N-oxide compound to the aliphatic primary alcohol is 0.0001 or more and 0.5 or less.

8. The N-oxyl compound and / or N-oxide compound is one or more selected from 2,2,6,6-tetramethylpiperidine N-oxyl, 1-methyl-2-azaadamantane-N-oxyl, 2-azaadamantane-N-oxyl, and N-methylmorpholine N-oxide. The manufacturing method according to claim 1.

9. The manufacturing method according to claim 1, wherein the temperature of the oxidation step is 60°C or higher and 200°C or lower.

10. The method for producing a primary alcohol according to claim 1, wherein the aliphatic primary alcohol having 4 or more carbon atoms is an aliphatic linear saturated primary alcohol having 8 to 14 carbon atoms.

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