# US 11,078,129 B2 · Method for producing olefin

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- Number: US 11,078,129 B2
- Document ID: US11078129B2
- Status: Granted
- Kind: B2
- Application number: 16/645,722
- Filed: 2018-05-29
- Published: 2020-09-24
- Granted: 2021-08-03
- Earliest claimed: 2017-09-12
- Assignees: Kao Corporation
- Applicants: Kao Corporation
- Inventors: Shingo Takada
- Web page: https://patentgrep.com/patent/US11078129B2

## CPC

- B01J 35/615: {100-500 m2/g}
- C07C 1/24: by elimination of water
- B01J 21/04: Alumina
- B01J 35/45: Nanoparticles
- B01J 35/633: {less than 0.5 ml/g}
- B01J 35/635: {0.5-1.0 ml/g}
- B01J 35/647: {2-50 nm}
- B01J 37/0018: {Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)}
- B01J 37/033: {Using Hydrolysis}
- B01J 37/088: {Decomposition of a metal salt}
- C07B 61/00: Other general methods
- C07C 11/02: Alkenes
- C07C 2521/04: Alumina
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention relates to a method for producing an olefin with a high yield for a short reaction time in a dehydration reaction of an aliphatic alcohol. The present invention provides a method for producing an olefin, including subjecting an aliphatic alcohol having 6 or more carbon atoms to a dehydration reaction in the presence of an aluminum oxide catalyst, wherein an average pore diameter of the aluminum oxide catalyst is 12.5 nm or more and 20.0 nm or less.

## Claims

### Claim 1

A method for producing an olefin, comprising subjecting an aliphatic alcohol having 6 or more carbon atoms to a dehydration reaction in the presence of a catalyst consisting of aluminum oxide, wherein
an average pore diameter of the catalyst is 12.5 nm or more and 20.0 nm or less, and
the catalyst is a powdered or granulated aggregate or is combined with a binder and molded.

### Claim 2 (depends on 1)

The method for producing an olefin according to claim 1, wherein the carbon number of the aliphatic alcohol is 8 or more and 22 or less.

### Claim 3 (depends on 1)

The method for producing an olefin according to claim 1, wherein the carbon number of the aliphatic alcohol is 14 or more and 18 or less.

### Claim 4 (depends on 1)

The method for producing an olefin according to claim 1, wherein the aliphatic alcohol is a primary alcohol.

### Claim 5 (depends on 1)

The method for producing an olefin according to claim 1, wherein the aliphatic alcohol is a straight-chain aliphatic alcohol.

### Claim 6 (depends on 1)

The method for producing an olefin according to claim 1, wherein the aliphatic alcohol is a saturated straight-chain aliphatic alcohol.

### Claim 7 (depends on 1)

The method for producing an olefin according to claim 1, wherein the amount of the catalyst used is 0.1 to 20 parts by mass based on 100 parts by mass of the aliphatic alcohol.

### Claim 8 (depends on 1)

The method for producing an olefin according to claim 1, wherein the catalyst is γ-alumina.

### Claim 9 (depends on 1)

The method for producing an olefin according to claim 1, wherein the average pore diameter of the catalyst is 13.0 nm or more and 20.0 nm or less.

### Claim 10 (depends on 1)

The method for producing an olefin according to claim 1, wherein the average pore diameter of the catalyst is 13.0 nm or more and 18.0 nm or less.

### Claim 11 (depends on 1)

The method for producing an olefin according to claim 1, wherein the average pore diameter of the catalyst is 13.5 nm or more and 16.0 nm or less.

### Claim 12 (depends on 1)

The method for producing an olefin according to claim 1, wherein a pore volume of the catalyst is more than 0.50 cm3/g and 2.0 cm3/g or less.

### Claim 13 (depends on 1)

The method for producing an olefin according to claim 1, wherein a BET specific surface area of the catalyst is 190 m2/g or more and 500 m2/g or less.

### Claim 14 (depends on 1)

The method for producing an olefin according to claim 1, wherein the dehydration reaction is performed at 200° C. or higher and 350° C. or lower.

### Claim 15 (depends on 1)

The method for producing an olefin according to claim 1, wherein the dehydration reaction is performed by a liquid phase reaction.

### Claim 16 (depends on 1)

The method for producing an olefin according to claim 1, wherein the dehydration reaction is performed in an inert gas atmosphere or a reducing atmosphere.