Method for producing nitrogen-containing organoxysilane compound

A method for producing a nitrogen-containing organoxysilane compound having a general formula (3) described below:

• wherein R1 and R2 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, the monovalent hydrocarbon group may include an oxygen, nitrogen, sulfur, or silicon atom in some cases, R1 and R2 may be bonded to each other to form a ring together with a nitrogen atom in some cases, and a case where both R1 and R2 are a hydrogen atom is excluded, R3 represents an unsubstituted divalent hydrocarbon group having 1 to 8 carbon atoms, R4 and R5 represent an unsubstituted monovalent hydrocarbon group having 1 to 6 carbon atoms, and m is an integer of 0, 1, or 2,
• wherein the nitrogen-containing organoxysilane compound having the general formula (3) is selected from:
• the method comprising the steps of:
• reacting an amine compound having a general formula (1) described below:
• wherein R1 and R2 are as described above,
• and wherein the amine compound having a general formula (1) is selected from:
• with a haloalkyl organoxysilane compound having a general formula (2) described below:
• wherein R3 to R5 and m are as described above, and X represents a halogen atom which is a chlorine atom;
• and wherein the haloalkyl organoxysilane compound having a general formula (2) is selected from:
• using 0.6 mol or more and 0.9 mol or less of a nitrogen-containing compound having a general formula (4) described below per 1 mol of the halogen atom in the haloalkyl organoxysilane compound having the general formula (2):
• wherein R6 represents an unsubstituted divalent hydrocarbon group having 2 to 5 carbon atoms, and A represents a single bond, —NH—, or —NCH3—;
• liquefying, by using a protic polar solvent, a mixture of the hydrogen halide salt of the amine compound having the general formula (1) and the hydrogen halide salt of the nitrogen-containing compound having the general formula (4) that are generated in the reaction system so as to obtain a reaction solution having two layers, so that one of the two layers contains the nitrogen-containing organoxysilane compound having the general formula (3);
• and
• removing the other of the two layers from the reaction solution, whereby separating the nitrogen-containing organoxysilane compound having the general formula (3) from the reaction solution,
• wherein the protic polar solvent is selected from the group consisting of methanol and ethanol.