Composite Catalyst for the Photocatalytic Isomerisation of Norbornadiene to Prepare Quadricyclane and Process for Making the Catalyst

Patent metadata

Field	Value
Publication number	US-2016339415-A1
Application number	US-201414648896-A
Country	US
Kind code	A1
Filing date	May 23, 2014
Priority date	Feb 17, 2014
Publication date	Nov 24, 2016
Grant date	—

Abstract

The present invention discloses a composite catalyst for the photocatalytic isomerisation of norbornadiene to prepare quadricyclane, comprising: a solid photocatalyst, selected from the group consisting of TiO 2 , Ti-MCM-41, Ti-SBA-15, ZnO, WO 3 , Ta 2 O 5 or SrTiO 3 ; and an organic photo-sensitizer loaded on the surface or in the channel of said solid photocatalyst, selected from benzophenone, acetophenone, Michler's Ketone, tetraethyl Michler's Ketone, and diethyl Michler's Ketone, where the organic photo-sensitizer is present in the solid photocatalyst in an amount of 0.5% to 20% by weight. The catalyst of the invention can catalyze a target reaction under the condition that no solvent is used, and the yield of the target product quadricyclane is higher. Furthermore, the catalyst of the invention has a stable activity, and it can be recycled. The invention further discloses a process for preparing the composite catalyst.

First claim

1 . A composite catalyst for photocatalystic isomerisation of norbornadiene to prepare quadricyclane, comprising:
a solid photocatalyst, selected from the group consisting of TiO 2 , Ti-MCM-41, Ti-SBA-15, ZnO, WO 3 , Ta 2 O 5 or SrTiO 3 ; and an organic photo-sensitizer loaded on the surface or in the channel of said solid photocatalyst, selected from benzophenone, acetophenone, Michler's Ketone, tetraethyl Michler's Ketone, or diethyl Michler's Ketone; where the organic photo-sensitizer is present in the solid photocatalyst in an amount of 0.5% to 20% by weight.

2 . The composite catalyst according to claim 1 , wherein said organic photo-sensitizer is bound to hydroxyl groups on the surface of channel of the solid photocatalyst.

3 . A process of preparing a composite catalyst for photocatalytic isomerisation of norbornadiene to prepare quadricyclane, comprising the steps:
(a) mixing a solution obtained by dissolving an organic photo-sensitizer in an organic solvent with a dried solid photocatalyst under sufficient stirring, wherein the weight ratio of the organic photo-sensitizer to the solid photocatalyst ranging from 0.5% to 20%, so that the organic photo-sensitizer is adsorbed onto the surface of the solid photocatalyst, wherein the solid photocatalyst is selected from TiO 2 , Ti-MCM-41, Ti-SBA-15, ZnO, WO 3 , Ta 2 O 5 or SrTiO 3 ; and the organic photo-sensitizer is selected from benzophenone, acetophenone, Michler's Ketone, tetraethyl Michler's Ketone, or diethyl Michler's Ketone; and (b) filtering off redundant solution and vacuum drying the solid photocatalyst which adsorbed the organic photo-sensitizer.

4 . The process according to claim 3 , wherein in the step a, the organic photo-sensitizer is present in the solution in a concentration of 20% by weight, and said solid photocatalyst is dried at 100° C., and said stirring continues for 24 hours; and in the step b, said vacuum drying is carried out at 100° C. for 5 hours.

Assignees

• Univ Tianjin

Inventors

• Zou Jijun
• Zhang Xiangwen
• Wang Li
• Wang Qingfa

Classifications

• C07C5/2266

  with hydrides or organic compounds (C07C5/2246 takes precedence) · CPC title

• C07C2531/36

  of vanadium, niobium or tantalum · CPC title

• B01J31/0271

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0231 · CPC title

• C07C2531/34

  of chromium, molybdenum or tungsten · CPC title

• C07C2103/86

  Chemistry & Metallurgy · mapped topic