BRPI0518466A2 - processes for the preparation of a hydroxide and a quaternary ammonium salt and, - Google Patents
processes for the preparation of a hydroxide and a quaternary ammonium salt and,Info
- Publication number
- BRPI0518466A2 BRPI0518466A2 BRPI0518466-5A BRPI0518466A BRPI0518466A2 BR PI0518466 A2 BRPI0518466 A2 BR PI0518466A2 BR PI0518466 A BRPI0518466 A BR PI0518466A BR PI0518466 A2 BRPI0518466 A2 BR PI0518466A2
- Authority
- BR
- Brazil
- Prior art keywords
- quaternary ammonium
- preparation
- hydroxide
- ammonium salt
- denatonium
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCESSOS PARA A PREPARAÇçO DE UM HIDRàXIDO E DE UM SAL DE AMâNIO QUATERNÁRIO, E, COMPOSTO. A invenção refere-se a um processo para a preparação de um hidróxido de amônio quaternário, particularmente hidróxido de denatônio, e ao seu uso para a preparação de um sal de amônio quaternário, particularmente de benzoato de denatônio ou um derivado de ácido graxo de denatônio. Devido a seu gosto extremamente amargo, este último composto é aplicado na arte como um agente aversivo, biocida, antiincrustante e flavorizante. Ele é geralmente preparado a partir de um halogeneto de amônio quaternário em um meio orgânico que, após isolamento e purificação, é convertido em um intermediário hidróxido higroscópico e instável, que, por sua vez, é imediatamente convertido no sal de interesse no solvente em que ele é preparado. Verificou-se agora que estas etapas de isolamento podem ser evitadas por realização da reação em condições aquosas. Isto é mais direto e não requer precauções onerosas para evitar contato enquanto manipulando. Além disso, o processo da invenção permite produzir sal de amônio quaternário a partir de um composto lignocaína em uma síntese em um vaso envolvendo principalmente água.PROCESSES FOR THE PREPARATION OF A HYDRAXIDE AND QUARTERLY AMMONIUM SALT, AND COMPOUND. The invention relates to a process for the preparation of a quaternary ammonium hydroxide, particularly denatonium hydroxide, and its use for the preparation of a quaternary ammonium salt, particularly denatonium benzoate or a denatonium fatty acid derivative. . Due to its extremely bitter taste, the latter compound is applied in the art as an aversive, biocidal, antifouling and flavoring agent. It is generally prepared from a quaternary ammonium halide in an organic medium which, after isolation and purification, is converted to a hygroscopic and unstable hydroxide intermediate, which in turn is immediately converted to the salt of interest in the solvent in which it is present. He is prepared. It has now been found that these isolation steps can be avoided by carrying out the reaction under aqueous conditions. This is more straightforward and requires no costly precautions to avoid contact while handling. Furthermore, the process of the invention allows to produce quaternary ammonium salt from a lignocaine compound in a pot synthesis involving mainly water.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63297604P | 2004-12-06 | 2004-12-06 | |
| EP04078299 | 2004-12-06 | ||
| PCT/NL2005/050055 WO2006062406A2 (en) | 2004-12-06 | 2005-11-30 | Preparation of a quaternary ammonium hydroxide and use thereof for the preparation of q quaternary ammonium salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0518466A2 true BRPI0518466A2 (en) | 2008-11-18 |
Family
ID=34928707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0518466-5A BRPI0518466A2 (en) | 2004-12-06 | 2005-11-30 | processes for the preparation of a hydroxide and a quaternary ammonium salt and, |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1824814A2 (en) |
| CN (1) | CN101111473A (en) |
| BR (1) | BRPI0518466A2 (en) |
| CA (1) | CA2591272A1 (en) |
| WO (1) | WO2006062406A2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102016009766A1 (en) | 2016-08-11 | 2018-02-15 | Julius-Maximilians-Universität Würzburg | Production of bitter substance derivatives |
| CN110354754A (en) * | 2019-07-10 | 2019-10-22 | 齐齐哈尔大学 | Amide bond quaternary cationics with different the morphology of the aggregate |
| CN112593078B (en) * | 2020-12-03 | 2022-08-05 | 江西理工大学 | Synthetic method of organic quaternary ammonium salt |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB955309A (en) * | 1959-11-20 | 1964-04-15 | Edinburgh Pharmaceutical Ind L | New quaternary salts and compositions containing them |
| GB8727504D0 (en) * | 1987-11-24 | 1987-12-23 | Glaxo Group Ltd | Chemical compositions |
| US5891919A (en) * | 1997-09-19 | 1999-04-06 | Burlington Bio-Medical & Scientific Corp. | Denatonium capsaicinate and methods of producing the same |
-
2005
- 2005-11-30 BR BRPI0518466-5A patent/BRPI0518466A2/en not_active Application Discontinuation
- 2005-11-30 WO PCT/NL2005/050055 patent/WO2006062406A2/en active Application Filing
- 2005-11-30 CA CA002591272A patent/CA2591272A1/en not_active Abandoned
- 2005-11-30 EP EP05809075A patent/EP1824814A2/en not_active Withdrawn
- 2005-11-30 CN CNA2005800475419A patent/CN101111473A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006062406A2 (en) | 2006-06-15 |
| WO2006062406A3 (en) | 2006-09-28 |
| CA2591272A1 (en) | 2006-06-15 |
| CN101111473A (en) | 2008-01-23 |
| EP1824814A2 (en) | 2007-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B11A | Dismissal acc. art.33 of ipl - examination not requested within 36 months of filing | ||
| B11Y | Definitive dismissal acc. article 33 of ipl - extension of time limit for request of examination expired |