IP Library Granted Patent US 9,393,554
Granted Patent B2
US 9,393,554 · App. 14/654,996 · Granted Jul 19, 2016

Method for producing saturated aldehyde from 1,2-alkanediol

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Quick Facts
Patent No.
US 9,393,554
App. No.
14/654,996
Granted
Jul 19, 2016
Kind
B2
Abstract

Provided is a method that produces a saturated aldehyde from a 1,2-alkanediol in high yield. Disclosed is a method for producing a saturated aldehyde from a 1,2-alkanediol in the presence of a regular mesoporous material.

Claims (20)

1. A method for producing a saturated aldehyde, the method comprising contacting a 1,2-alkanediol with a regular mesoporous material to convert the 1,2-alkanediol into a saturated aldehyde, wherein the regular mesoporous material is a regular mesoporous material obtained by reacting a layered silicate with a surfactant.

2. The method according to claim 1 , wherein an average pore size of the regular mesoporous material is 2.0 nm or more and 10.0 nm or less.

3. The method according to claim 1 , wherein an acid quantity of the regular mesoporous material is 1.0 mmol/g or more and 10.0 mmol/g or less.

4. The method according to claim 1 , wherein the layered silicate is selected from kanemite (NaHSi 2 O 5 .3H 2 O), sodium disilicate crystals (α, β, γ, σ-Na 2 Si 2 O 5 ), makatite (Na 2 Si 4 O 9 .5H 2 O), ilerite (Na 2 Si 8 O 17 .xH 2 O), magadiite (Na 2 Si 14 O 29 .xH 2 O), and kenyaite (Na 2 Si 20 O 41 .xH 2 O).

5. The method according to claim 1 , wherein the regular mesoporous material is FSM-16.

6. The method according to claim 1 , wherein the 1,2-alkanediol is 1,2-propanediol.

7. The method according to claim 1 , wherein the saturated aldehyde is propionaldehyde.

8. The method according to claim 1 , wherein the 1,2-alkanediol is contacted with a regular mesoporous material such that W/F is 0.01 g·min/ml or more and 1000 g·min/ml or less.

9. The method according to claim 1 , wherein a temperature of the regular mesoporous material during the contacting is set to 200° C. or higher and 800° C. or lower.

10. The method according to claim 1 , wherein

the 1,2-alkanediol is 1,2-propanediol,

the saturated aldehyde is propionaldehyde,

the 1,2-propanediol is contacted with the regular mesoporous material such that W/F is 0.01 g·min/ml or more and 1000 g·min/ml or less,

a temperature of the regular mesoporous material during the contacting is set to 200° C. or higher and 800° C. or lower, and

the yield of propionaldehyde is at least 42.5%.

11. The method according to claim 10 , wherein the regular mesoporous material is FSM-16.

12. The method according to claim 10 , wherein the regular mesoporous material is MCM-41.

13. The method according to claim 1 , wherein the yield of saturated aldehyde is at least 42.5%.

14. The method according to claim 1 , wherein the yield of saturated aldehyde is at least 42.5%-63.0%.

15. The method according to claim 10 , wherein the yield of propionaldehyde is 42.5%-63.0%.

Assignments (2)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2015
From: SUGIYAMA, SHIGERU; KATOU, YUUKI; YASUKAWA, TOSHIYA; AKIHARA, SHUJI; NINOMIYA, WATARU
To: TOKUSHIMA UNIVERSITY; MITSUBISHI RAYON CO., LTD.
Reel/Frame 035960/0372 →