Process for synthesizing O-substituted oxime compounds and conversion to the corresponding O-substituted hydroxylamine

A process for the preparation of aminooxyacetic acid which comprises:

• (a) reacting an alkali metal or alkaline earth metal hydroxide compound and a solution of an oxime compound to form a first mixture comprising the alkali metal or alkaline earth metal salt of said oxime compound and water;
• (b) adding a haloacetic acid while stirring to said first mixture to form a second mixture comprising oxime-O-acetic acid, the alkali metal or alkaline earth metal salt of said oxime compound, water, unreacted haloacetic acid and excess oxime compound;
• (c) heating said second mixture in the presence of an amount of water sufficient to react hydroxide with said unreacted haloacetic acid to obtain oxime-O-acetic acid free of unreacted haloacetic acid;
• and
• (d) hydrolyzing said oxime-O-acetic acid to aminooxyacetic acid.

A process consisting of:

• (a) reacting an alkali metal or alkaline earth metal hydroxide compound and a solution of an oxime compound in an excess of said oxime compound to form a first mixture comprising the alkali metal or alkaline earth metal salt of said oxime compound and water;
• (b) adding a haloacetic acid while stirring to said first mixture to form a second mixture comprising an oxime-O-acetic acid, the alkali metal or alkaline earth metal salt of said oxime compound, water, unreacted haloacetic acid and excess oxime compound;
• (c) heating said second mixture in the presence of an amount of water sufficient to react hydroxide with said unreacted haloacetic acid to obtain an oxime-O-acetic acid free of unreacted haloacetic acid;
• and
• (d) hydrolyzing said oxime-O-acetic acid to form aminooxyacetic acid.

A process which comprises:

• (a) reacting an alkali metal or alkaline earth metal hydroxide compound and a solution of an oxime compound in an excess of said oxime compound to form a first mixture comprising the alkali metal or alkaline earth metal salt of said oxime compound and water;
• (b) adding a haloacetic acid while stirring to said first mixture to form a second mixture comprising an oxime-O-acetic acid, the alkali metal or alkaline earth metal salt of said oxime compound, water, unreacted haloacetic acid and excess oxime compound, and not subjecting said first mixture to azeotropic distillation, to remove all or a portion of the water from said first mixture;
• and
• (c) heating said second mixture in the presence of an amount of water sufficient to react hydroxide with said unreacted haloacetic acid to obtain an oxime-O-acetic acid free of unreacted haloacetic acid.