Method for producing indancarbaldehyde

Patent metadata

Field	Value
Publication number	US-10737993-B2
Application number	US-201816605628-A
Country	US
Kind code	B2
Filing date	Mar 9, 2018
Priority date	Apr 18, 2017
Publication date	Aug 11, 2020
Grant date	Aug 11, 2020

Abstract

The present invention provides a method for producing indancarbaldehyde, including a step of reacting indan with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride to obtain a reaction liquid including indancarbaldehyde, wherein
the indan includes an amine, and a content of the amine is less than 1000 ppm by mass.

First claim

The invention claimed is:

1. A method for producing indancarbaldehyde, comprising:
reacting indan with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride to obtain a reaction liquid comprising indancarbaldehyde, wherein
the indan comprises an amine, and a content of the amine is less than 1000 ppm by mass.

2. The method for producing indancarbaldehyde according to claim 1 , wherein the indan is a reaction product of a hydrogenation reaction of a raw material comprising indene.

3. The method for producing indancarbaldehyde according to claim 2 , wherein a content of the indene contained in the raw material is 90% by mass or more.

4. The method for producing indancarbaldehyde according to claim 2 , wherein the raw material comprising the indene comprises benzonitrile, and
a content of the benzonitrile is 0.5 to 10% by mass.

5. The method for producing indancarbaldehyde according to claim 1 , wherein the indan comprises benzonitrile, and
a content of the benzonitrile is 0.5 to 10% by mass.

6. The method for producing indancarbaldehyde according to claim 1 , wherein the indancarbaldehyde is indan-5-carbaldehyde represented by formula (1):

7. The method for producing indancarbaldehyde according to claim 1 , wherein the amine contained in the indan is at least one selected from the group consisting of benzylamine, dibenzylamine, and tribenzylamine.

8. The method for producing indancarbaldehyde according to claim 1 , further comprising:
adding a heat medium to the reaction liquid comprising the indancarbaldehyde followed by heating for separation into a flow comprising the hydrogen fluoride and the boron trifluoride and a flow comprising the indancarbaldehyde and the heat medium.

9. The method for producing indancarbaldehyde according to claim 8 , wherein the heating is performed under conditions of a temperature of 120 to 180° C. and 0.1 to 1.0 MPa in terms of gauge pressure.

10. The method for producing indancarbaldehyde according to claim 1 , further comprising:
reducing a raw material comprising indene in the presence of a catalyst and hydrogen to obtain a reaction product comprising indan, and
distilling and purifying the reaction product comprising the indan to obtain indan having a content of an amine of less than 1000 ppm by mass.

11. The method for producing indancarbaldehyde according to claim 10 , wherein the reduction is performed under conditions of a temperature of 20 to 100° C. and normal pressure to 2.0 MPa in terms of gauge pressure.

12. The method for producing indancarbaldehyde according to claim 10 , wherein the catalyst comprises palladium and/or platinum.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Utamura Tatsuya

Classifications

• C07C45/49 Primary

  by reaction with carbon monoxide · CPC title

• C07C47/546

  polycyclic · CPC title

• C07C45/86

  Use of additives, e.g. for stabilisation · CPC title

• C07C45/82

  by distillation · CPC title

• C07C5/03 Primary

  of non-aromatic carbon-to-carbon double bonds · CPC title