Preparation method for an imine compound and reduction method for solid powder of a carbamic acid derivative

Patent metadata

Field	Value
Publication number	US-9346772-B2
Application number	US-201514823682-A
Country	US
Kind code	B2
Filing date	Aug 11, 2015
Priority date	Feb 14, 2011
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

The present application relates to a preparation method for solid powder of a carbamic acid derivative, which includes reacting an amine derivative with carbon dioxide at a temperature in a range of from about −30° C. to about 500° C. and at a pressure in a range of from about 0.3 MPa to about 100 MPa. In addition, the present disclosure relates to a reduction method for solid powder of a carbamic acid derivative to an amine derivative and carbon dioxide, which includes dissolving solid powder of the carbamic acid derivative prepared in a solvent; refluxing the carbamic acid derivative at a temperature in a range of from about 30° C. to about 100° C.; and evaporating the solvent.

First claim

What is claimed is:

1. A preparation method for an imine compound, comprising:
reacting an amine derivative with carbon dioxide at a temperature in a range of from about −30° C. to about 500° C. and at a pressure in a range of from about 0.3 MPa to about 100 MPa to obtain solid powder of a carbamic acid derivative; and
reacting the solid powder of the carbamic acid derivative with an aldehyde to obtain an imine compound.

2. The preparation method for an imine compound of claim 1 , wherein the reaction of the solid powder of the carbamic acid derivative with the aldehyde is performed without using a solvent.

3. The preparation method of claim 1 , wherein the solid powder of the carbamic acid derivative includes a compound represented by the following Chemical Formula 3, Chemical Formula 3′, or Chemical Formula 4:

wherein in Chemical Formulas 3, 3′, or 4, each of R 1 , R 2 , R 3 and R 4 is independently hydrogen; a C 1-30 alkyl group substituted or non-substituted with nitrogen; a C 6-30 aryl group substituted or non-substituted with nitrogen; or a C 3-30 cycloalkyl group substituted or non-substituted with nitrogen, and
R 5 is a C 2-30 alkyl group substituted or non-substituted with nitrogen; a C 6-30 aryl group substituted or non-substituted with nitrogen; or a C 3-30 cycloalkyl group substituted or non-substituted with nitrogen.

4. The preparation method of claim 1 , wherein the aldehyde include a C 1 -C 12 compound containing an aldehyde group.

5. The preparation method of claim 1 , wherein the aldehyde is an C 1 -C 12 alkyl aldehyde or an C 6 -C 12 arylaldehyde.

Assignees

• Univ Sogang Res Foundation

Inventors

• Hur Nam Hwi
• Lee Byeong No

Classifications

• C07D295/13 Primary

  to an acyclic saturated chain · CPC title

• C07C209/62

  by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds (C07C209/24 takes precedence) · CPC title

• C07B43/00

  Formation or introduction of functional groups containing nitrogen · CPC title

• C07C269/04

  from amines with formation of carbamate groups · CPC title

• C07C209/00

  Preparation of compounds containing amino groups bound to a carbon skeleton · CPC title