Processes for producing methenamine mandelate

Patent metadata

Field	Value
Publication number	US-10683303-B2
Application number	US-201716306719-A
Country	US
Kind code	B2
Filing date	May 26, 2017
Priority date	Jun 3, 2016
Publication date	Jun 16, 2020
Grant date	Jun 16, 2020

Abstract

Processes are provided for the production of methenamine mandelate that do not require the isolation of produced methenamine prior to production of the methenamine mandelate.

First claim

What is claimed is:

1. A process comprising:
bubbling ammonia through a first combination comprising paraformaldehyde, a first C2-C6 alcohol, and water, while maintaining the first combination at about 20 deg. C. to about 90 deg. C., thereby producing a first reaction product comprising methenamine;
combining at least the first reaction product, mandelic acid, and a second C2-C6 alcohol under heat, thereby producing a second reaction product;
heating the second reaction product to a temperature of about 20 deg. C. to about 100 deg. C.; and
cooling the second reaction product to at least about 70 deg. C.,
thereby producing a composition comprising methenamine mandelate.

2. A process as in claim 1 wherein the first C2-C6 alcohol comprises n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

3. A process as in claim 1 wherein the second C2-C6 alcohol comprises as isopropanol, n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

4. A composition comprising methenamine mandelate, wherein the methenamine mandelate is prepared by a process comprising:
bubbling ammonia through a first combination comprising paraformaldehyde, a first C2-C6 alcohol, and water, while maintaining the first combination at about 20 deg. C. to about 90 deg. C., thereby producing a first reaction product comprising methenamine;
combining at least the first reaction product, mandelic acid, and a second C2-C6 alcohol under heat, thereby producing a second reaction product;
heating the second reaction product to a temperature of about 20 deg. C. to about 100 deg. C.; and
cooling the second reaction product to at least about 70 deg. C.,
thereby producing a composition comprising methenamine mandelate.

5. The composition of claim 1 , wherein the first C2-C6 alcohol comprises n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

6. The composition of claim 1 , wherein the second C2-C6 alcohol comprises as isopropanol, n-butanol, cyclohexanol, n-propanol, isopropanol, n-pentanol, n-hexanol, isobutanol, s-butanol, or t-butanol.

Assignees

• Albemarle Corp

Inventors

• Assink Bryce Kelly
• Caviggiola Iii Tino Jon

Classifications

• C07D487/18

  Bridged systems · CPC title

• C07C51/41

  Preparation of salts of carboxylic acids ({C07C51/093 - C07C51/34 take precedence} preparation of soap C11D) · CPC title

• C07C51/412

  by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part · CPC title

• A61P13/02

  of urine or of the urinary tract, e.g. urine acidifiers · CPC title

• C07D487/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title