# US 5,332,826 A · Process for preparing aminoacetonitriles in one vessel

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- Number: US 5,332,826 A
- Document ID: US5332826A
- Status: Granted
- Kind: A
- Application number: 08/136,432
- Filed: 1993-10-13
- Granted: 1994-07-26
- Earliest claimed: 1993-10-13
- Assignees: Eastman Kodak Company
- Inventors: Paul R. Buckland
- Web page: https://patentgrep.com/patent/US5332826A

## CPC

- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07C 253/00: Preparation of carboxylic acid nitriles (of cyanogen or compounds thereof C01C3/00)
- C07C 253/30: by reactions not involving the formation of cyano groups
- C07D 213/57: Nitriles
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

This invention relates to a process for preparing aminoacetonitriles in one vessel. The process involves the steps of: (A) reacting an alkali metal cyanide with an aldehyde in water to form a cyanohydrin; (B) extracting the cyanohydrin formed in Step (A) into a water immiscible solvent to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase; (C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin; (D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution; and (E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.

## Claims

### Claim 1

A process for preparing aminoacetonitriles comprising the steps of:
(A) reacting an alkali metalcyanide with an aldehyde having the formula RCHO at a temperature of -10.degree. C. to 25.degree. C. in water to form a cyanohydrin, wherein R is selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.3 -C.sub.8 alkynyl, and C.sub.6 -C.sub.14 aryl, excluding 3-nitrobenzaldehyde;
(B) adding a water immiscible solvent to the cyanohydrin formed in Step (A) to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase;
(C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin;
(D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution; and
(E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile,
provided steps (B), (C), (D), and (E) are conducted at a temperature of 20.degree. C. to 50.degree. C, and further provided that steps (A), (B), (C), (D), and (E) are conducted in the same reaction vessel wherein the cyanohydrin is not isolated.

### Claim 2

A process for preparing aminoacetonitriles comprising the steps of:
(A) reacting an alkali metal cyanide with an aldehyde at a temperature of -10.degree. C. to 25.degree. C. in water to form a cyanohydrin, wherein the alkali metal cyanide is selected from the group consisting of sodium cyanide, potassium cyanide, lithium cyanide and cesium cyanide, and the aldehyde is selected from the group consisting of p-anisaldehyde, thiophene-2-carboxaldehyde, furan-2-carboxaldehyde, benzaldehyde, crotonaldehyde, trimethylacetaldehyde, acetaldehyde, 4-methylbenzaldehyde, 4N,N-dimethylaminobenzaldehyde, 3-pyridinecarboxaldehyde, valeraldehyde, and 2-chlorobenzaldehyde;
(B) adding a water immiscible solvent to the cyanohydrin formed in Step (A) to from a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase, wherein the water immiscible solvent is selected from the group consisting of dichloromethane, ethyl acetate, diethyl ether, chloroform, 1,2-dichloroethane, methyl acetate, propyl acetate, methyl propionate, methyl butyrate, dimethyl malonate, isobutyl acetate, methylisobutyl ketone, and combinations thereof; removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin;
(D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution, wherein the water miscible amide solvent is selected from the group consisting of N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide, N,N-dimethylpropionamide, N,N-diethylpropionamide, formamide, and combinations thereof; and
(E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile,
provided steps (B), (C), (D), and (E) are conducted at a temperature of 20.degree. C. to 50.degree. C., and further provided that steps (A), (B), (C), (D), and (E) are conducted in the same reaction vessel wherein the cyanohydrin is not isolated.

### Claim 3

A process for preparing aminoacetonitriles comprising the steps of:
(A) reacting an alkali metal cyanide with 3-pyridinecarboxaldehyde at a temperature of -5.degree. C. to 5.degree. C. in water to form a cyanohydrin, wherein the alkali metal cyanide is selected from the group consisting of sodium cyanide and potassium cyanide;
(B) adding a water immiscible solvent to the cyanohydrin formed in Step (A) to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase, wherein the water immiscible solvent is selected from the group consisting of dichloromethane and ethyl acetate;
(C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin;
(D) adding N,N-dimethylformamide to the concentrated cyanohydrin to form a cyanohydrin solution; and
(E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile,
provided steps (B), (C), (D), and (E) are conducted at a temperature of 30.degree. C. to 40.degree. C., and further provided the steps (A), (B), (C), (D), and (E) are conducted in the same reaction vessel wherein the cyanohydrin is not isolated.