Method for producing olefin

Patent metadata

Field	Value
Publication number	US-9968914-B2
Application number	US-201314655534-A
Country	US
Kind code	B2
Filing date	Dec 19, 2013
Priority date	Dec 26, 2012
Publication date	May 15, 2018
Grant date	May 15, 2018

Abstract

The present invention relates to a process for producing olefins, including the step of subjecting an alcohol having not less than 8 and not more than 22 carbon atoms to dehydration reaction in the presence of a solid acid catalyst, in which the solid acid catalyst includes aluminum oxide and an oxide of an element having an electronegativity higher than that of aluminum which is supported on the aluminum oxide.

First claim

The invention claimed is:

1. A process for producing olefins, comprising the step of subjecting an alcohol having not less than 8 and not more than 22 carbon atoms to dehydration reaction in the presence of a solid acid catalyst, in which the solid acid catalyst comprises aluminum oxide and an oxide of an element having an electronegativity higher than that of aluminum which is supported on the aluminum oxide,
wherein the dehydration reaction is a liquid phase reaction,
wherein the element is at least one element selected from the group consisting of sulfur, tungsten, and phosphorus,
wherein an amount of the oxide of the element supported on the aluminum oxide is not less than 0.8% by mass and not more than 5% by mass on the basis of the amount of the aluminum oxide, and
wherein the dehydration reaction is carried out at a temperature of not lower than 200° C. and not higher than 310° C.

2. The process for producing olefins according to claim 1 , wherein the aluminum oxide is γ-alumina.

3. The process for producing olefins according to claim 1 , wherein the alcohol is a primary alcohol.

4. The process for producing olefins according to claim 1 , wherein the alcohol is at least one alcohol selected from the group consisting of 1-dodecanol, 1-tridecanol, 1-tetradecanol, 1-pentadecanol, 1-hexadecanol, 1-heptadecanol, 1-octadecanol, 1-nonadecanol and 1-eicosanol.

5. The process for producing olefins according to claim 1 , wherein a method of producing the catalyst by supporting the oxide of the element on the aluminum oxide comprises the steps of mixing an aqueous suspension or a hydrous solid of the aluminum oxide, a compound as an oxide source of the element or the oxide of the element, and ion-exchanged water to prepare an impregnated product, and drying and calcining the resulting impregnated product.

6. The process for producing olefins according to claim 5 , wherein the compound as an oxide source of the element is a water-soluble ammonium salt, a metal alkoxide, or an oxo acid or a salt thereof.

7. The process for producing olefins according to claim 5 , wherein the compound as an oxide source of the element is ammonium sulfate, ammonium tungstate or diammonium hydrogen phosphate.

8. The process for producing olefins according to claim 1 , wherein the dehydration reaction is carried out while removing water produced therein out of the reaction system.

9. The process for producing olefins according to claim 8 , wherein the dehydration reaction is carried out while introducing an inert gas into the reaction system.

10. The process for producing olefins according to claim 1 , wherein the BET specific surface area of the catalyst is not less than 100 m 2 /g and not more than 500 m 2 /g.

11. The process for producing olefins according to claim 1 , wherein the average pore size of the catalyst is not less than 5 nm and not more than 50 nm.

12. The process for producing olefins according to claim 1 , wherein the pore volume of the catalyst is not less than 0.20 cm 3 /g and not more than 2.0 cm 3 /g.

13. A process for producing an olefin sulfonate, comprising the steps of:
sulfonating the olefins produced by the process as claimed in claim 1 to obtain a sulfonated product; and
neutralizing the sulfonated product and then subjecting the resulting neutralized product to hydrolysis treatment.

14. A process for producing olefins, comprising the step of subjecting an alcohol having not less than 8 and not more than 22 carbon atoms to dehydration reaction in the presence of a solid acid catalyst, in which the solid acid catalyst comprises aluminum oxide and an oxide of an element having an electronegativity higher than that of aluminum which is supported on the aluminum oxide,
wherein an amount of the oxide of the element supported on the aluminum oxide is not less than 0.8% by mass and not more than 5% by mass on the basis of the aluminum oxide,
wherein the dehydration reaction is a liquid phase reaction,
wherein a method of producing the catalyst by supporting the oxide of the element on the aluminum oxide comprises the steps of mixing an aqueous suspension or a hydrous solid of the aluminum oxide, a compound as an oxide source of the element or the oxide of the element, and ion-exchanged water to prepare an impregnated product, and drying and calcining the resulting impregnated product,
wherein the dehydration reaction is carried out at a temperature of not lower than 200° C. and not higher than 310° C., and
wherein the process does not utilize an organic solvent therein.

15. The process for producing olefins according to claim 14 ,
wherein the alcohol is at least one alcohol selected from the group consisting of 1-dodecanol, 1-tridecanol, 1-tetradecanol, 1-pentadecanol, 1-hexadecanol, 1-heptadecanol, 1-octadecanol, 1-nonadecanol and 1-eicosanol, and
wherein the compound as an oxide source of the element is ammonium sulfate, ammonium tungstate, diammonium hydrogen phosphate or tetraethyl orthosilicate.

Assignees

• Kao Corp

Inventors

• Takada Shingo

Classifications

• C07C2521/06

  Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof · CPC title

• C07C1/24

  by elimination of water · CPC title

• B01J27/053 Primary

  Sulfates · CPC title

• B01J23/10

  of rare earths · CPC title

• C07C2527/167

  Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)- · CPC title