US 2002/0058834 A1 · Preparation of N-acyl amino carboxylic acids, amino carboxylic acids and their derivatives by metal-catalyzed carboxymethylation in the presence of a promoter

Abstract

A process for the preparation of amino carboxylic acids, N-acyl amino carboxylic acids, or derivatives thereof by carboxymethylation of an amide, amide precursor or amide source compound in the presence of a carboxymethylation catalyst precursor and a promoter is provided. A carboxymethylation reaction mixture is formed by introducing a promoter, an amide, amide precursor or amide source compound, carbon monoxide, hydrogen, an aldehyde or aldehyde source compound, and a carboxymethylation catalyst precursor into a carboxymethylation reaction zone. In a preferred embodiment, the promoter is a supported noble metal promoter. In another preferred embodiment, the amide compound and aldehyde are selected to yield an N-acyl amino carboxylic acid which is readily converted to N-phosphonomethyl)glycine, or a salt or ester thereof.

Claims122

Dependent claims

A process for the preparation of an amino carboxylic acid or a derivative thereof by carboxymethylation of an amide, an amide precursor or an amide source compound, the process comprising:

introducing a carboxymethylation catalyst precursor, a promoter for conversion of the carboxymethylation catalyst precursor to an active catalyst species, an aldehyde or an aldehyde source compound, carbon monoxide, hydrogen and the amide, amide precursor or amide source compound into a carboxymethylation reaction zone to form a carboxymethylation reaction mixture;
and
heating the carboxymethylation reaction mixture under pressure to produce a carboxymethylation product mixture containing an amino carboxylic acid product, a catalyst precursor reaction product and the promoter.

A process for the preparation of an amino carboxylic acid or a derivative thereof by carboxymethylation of an amide compound, the process comprising:

introducing a carboxymethylation catalyst precursor, a promoter for converting the carboxymethylation catalyst precursor to an active catalyst species, carbon monoxide, hydrogen, an aldehyde or an aldehyde source compound, and said amide compound into a carboxymethylation reaction zone to form a carboxymethylation reaction mixture;
heating the carboxymethylation reaction mixture under pressure to produce a carboxymethylation product mixture containing an N-acyl amino carboxylic acid product, a catalyst precursor reaction product, and the promoter;
recovering the promoter from said carboxymethylation product mixture;
recovering the catalyst precursor reaction product from said carboxymethylation product mixture;
and
regenerating the carboxymethylation catalyst precursor from said recovered catalyst precursor reaction product in the presence of said amide compound,
said amide compound comprising a carbamoyl compound having the formula;
41
wherein
R1 is selected from the group consisting of hydrocarbyl and substituted hydrocarbyl;
and
R2 and R2a are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
provided, however, that at least one of R2 and R2a is a group which undergoes carbonylation under the conditions of the carboxymethylation reaction.

10 more elements

A process for the preparation of an amino carboxylic acid or a derivative thereof by carboxymethylation of an amide compound, the process comprising:

introducing a carboxymethylation catalyst precursor, a promoter for conversion of the carboxymethylation catalyst precursor to an active catalyst species, carbon monoxide, hydrogen, an aldehyde or an aldehyde source compound, and said amide compound into a carboxymethylation reaction zone to form a carboxymethylation reaction mixture;
heating the carboxymethylation reaction mixture under pressure to produce a carboxymethylation product mixture containing an amino carboxylic acid product, a catalyst precursor reaction product, and the promoter;
said amide compound comprising a sulfonamide or sulfinamide compound having the formula;
42
wherein;
R1 is selected from the group consisting of hydrocarbyl, substituted hydrocarbyl, and NR3R4;
R2 and R2a are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
and
R3 and R4 are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
provided, however, that at least one of R2 and R2a is a group which undergoes carbonylation under the conditions of the carboxymethylation reaction;
or R1 is —NR3R4 and at least one of R3 and R4 is a group which undergoes carbonylation under the conditions of the carboxymethylation reaction.

8 more elements

A process for the preparation of N-(phosphonomethyl)glycine, a salt of N-(phosphonomethyl)glycine, or an ester of N-(phosphonomethyl)glycine, the process comprising:

preparing an N-acyl amino carboxylic acid product by carboxymethylating a carbamoyl compound in a carboxymethylation reaction mixture formed by introducing said carbamoyl compound, formaldehyde, carbon monoxide, hydrogen, a carboxymethylation catalyst precursor comprising cobalt and a supported metallic promoter into a carboxymethylation reaction zone;
converting the N-acyl amino carboxylic acid product to N-(phosphonomethyl)glycine, a salt of N-(phosphonomethyl)glycine, or an ester of N-(phosphonomethyl)glycine wherein said conversion comprises deacylating the N-acyl amino carboxylic acid product to generate a carboxylic acid and an amino acid;
and
reacting the carboxylic acid with an amine to generate the carbamoyl compound or a compound from which the carbamoyl compound may be derived;
said carbamoyl compound having the formula:
43
wherein;
R1 is selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, NR3R4, OR5, and SR6;
R2 and R2a are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
R3 and R4 are independently selected from the group consisting of hydrogen, hydrocarbyl, and substituted hydrocarbyl;
and
R5 and R6 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and a salt-forming cation;
provided, however, that at least one of R2 and R2a is a group which undergoes carbonylation under the conditions of the carboxymethylation reaction;
or R1 is —NR3R4 and at least one of R3 and R4 is a group which undergoes carbonylation under the conditions of carboxymethylation reaction.

11 more elements

Dependencies are inferred from the claim text.

Preparation of N-acyl amino carboxylic acids, amino carboxylic acids and their derivatives by metal-catalyzed carboxymethylation in the presence of a promoter

Life of this patent

Preparation of N-acyl amino carboxylic acids, amino carboxylic acids and their derivatives by metal-catalyzed carboxymethylation in the presence of a promoter

Life of this patent

Abstract

Claims122