Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Destruction of hazardous or toxic waste
Reexamination Certificate
2000-06-06
2003-06-24
Marx, Irene (Department: 1651)
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Destruction of hazardous or toxic waste
C435S252500, C435S170000, C435S121000
Reexamination Certificate
active
06582952
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
This invention relates to a method for the removal of a nitrogen containing heterocyclic or aromatic compound, comprising at least one nitro group. The method of the invention consists of converting at least one nitro group into an amine group by means of a reducing agent. The reducing agent can be a micro-organism capable of reducing said, at least one nitro group into an amine group, or can be hydrogen in the presence of a Pd/C catalyst.
This invention also relates to a method for the synthesis of 5-amino-1,2,4-triazole-3-one from 5-nitro-1,2,4-triazole-3-one by said method of conversion.
This invention also relates to a colony of the type
Bacillus licheniformis
capable of converting one or more nitro groups of nitrogen containing heterocyclic compounds into one or more amine groups.
The nitrogen containing heterocyclic compound can be, for example, a triazine or a triazole. These compounds constitute a heterogeneous family of nitrogen containing molecules several of which are used in industry and in agriculture. Although the toxicity of these compounds has not always been given prominence, they can nevertheless constitute a source of pollution, when released into the natural environment.
An example of such a compound is ONTA or 1,2-dihydro-5-nitro-1,2,4-triazole-3-one. This compound is explosive and it can reach concentrations of about 15 g/l in certain solutions such as industrial processing effluents stemming from the manufacture of explosives. These effluents are pollutants according to the legislation currently in force and are at present being stored in this state while awaiting a suitable treatment process.
The method of the invention enables precisely such solutions to be treated, solutions comprising, in particular, a compound such as ONTA, that is to say an explosive nitrogen containing heterocyclic compound, comprising at least one nitro group, by converting this explosive nitrogen containing heterocyclic compound into a non-explosive compound.
In the example mentioned above, the method of the invention allows one to convert the nitro group of the ONTA into an amine group to form 5-amino-1,2,4-triazole-3-one.
Furthermore, the 5-amino-1,2,4-triazole-3-one formed is a compound of value, since it can be a precursor for the synthesis of compounds, having, for example antiviral activity such as ribavirine, and pirazomicine, an inhibiting activity for the NO-synthases (NO.S.) such as 3-amino-1,2,4-triazine and aminoguanidine, a herbicide activity such as 5-amino-1,2,4-triazole, an anti-parasitic activity and a cytotoxic activity.
The method of the invention therefore makes it possible, in certain cases to convert a compound of no value into a compound of value.
Another aspect of the method of the invention is the synthesis of the heterocyclic amine 5-amino-1,2,4-triazole-3-one from 5-nitro-1,2,4-triazole-3-one.
The aromatic compound comprising at least one nitro group can be, for example, a benzene ring with one or more nitro groups, for example a compound chosen from the group comprising 2,6-dinitroaniline, 1,3-dinitrobenzene, 2-nitroaniline and ortho-, meta- and para-nitrobenzoic acids.
The aromatic amines and nitrogen containing heterocyclic amines are often obtained by reduction of the nitrated analogue. This reduction is catalyzed by various methods using reducing agents such as zinc, iron or tin, in an acid medium or hydrides such as lithium aluminum hydride, or catalytic hydrogenation. However, when the aromatic amines are complex, that is to say when they include sensitive functional groups apart from the nitro group, numerous secondary reactions can occur on these groups that then reduces the yield of the synthesis of the targeted aromatic amine.
For example, the reduction of ONTA by catalytic hydrogenation in the presence of platinum oxide can affect the aromaticity of the molecule in addition to the nitro group.
Furthermore, the experimental conditions for these synthesis methods are often drastic and dangerous.
DESCRIPTION OF THE INVENTION
This invention relates to a method for the at least partial removal of at least one nitrogen containing heterocyclic compound or aromatic compound comprising at least one nitro group, present in an effluent, said method comprising the following steps:
bringing the solution of the nitrogen containing heterocyclic compound or aromatic compound to be removed into contact with a reducing agent in order to convert said nitro group or groups of the heterocyclic compound or aromatic compound into one or more amine groups, and
separation of the reducing agent from the solution of the nitrogen containing heterocyclic compound or aromatic compound, at least a part of whose nitro groups has been converted into amine groups.
According to the method of the invention, the solution of the nitrogen containing heterocyclic compound or aromatic compound comprising at least one nitro group can contain a single compound or several different compounds. This solution can be an industrial processing effluent arising from the manufacture of explosives, an industrial effluent, foul water and more generally a solution comprising nitrogen containing heterocyclic compounds or aromatic compounds comprising at least one nitro group that it is necessary to treat by converting one or more nitro groups into amine groups. This solution will also be referred to in what follows as the solution to be treated, and the nitrogen containing heterocyclic compound or aromatic compound comprising at least one nitro group will also be referred to in what follows, respectively as a nitrogen containing heterocyclic compound to be treated or an aromatic compound to be treated.
According to the method of the invention, the reducing agent can be hydrogen in the presence of a Pd/C catalyst.
The hydrogenation catalyst Pd/C, or palladium on carbon, can be used at a quantity of from 5 to 15% by weight with respect to the quantity of nitrogen containing heterocyclic compound or aromatic compound to be removed, preferably at a quantity of 10% by weight. The effluent can, for example, be an aqueous solution or methanol.
According to the method of the invention, the reducing agent can be a micro-organism.
According to the method of the invention, the nitrogen containing heterocyclic compound comprising at least one nitro group can be a triazole.
According to the method of the invention, when the nitrogen containing heterocyclic compound to be treated is a triazole, it can be a compound with the following formula (I):
in which the R
1
and R
2
groups, which can be identical or different, represent H, or a substituent group chosen from within the group comprising —NO
2
, —OH, —COOH, —Cl, —NH
2
, or a cyclic or linear glucose unit, non-substituted or substituted by one or more groups chosen independently from within the group comprising for example an acetyl or a tolyl group or a linear or cyclic alkyl group, comprising from 1 to 10 atoms of carbon, non-substituted or substituted by one or more groups chosen independently from within the group comprising —NO
2
, —OH, —COOH, —Cl, —NH
2
. For example, when R
1
and/or R
2
is a glucose unit, it can be ribose, deoxyribose, etc non-substituted or substituted.
According to the method of the invention, the compound of formula (I) can be converted into a compound with the following formula (II):
in which the groups R
3
and R
4
, which can be identical or different, represent H, a substituent group chosen from within the group comprising —NO
2
, —OH, —COOH, —Cl, —NH
2
, or a cyclic or linear glucose unit, non-substituted or substituted by one or more groups chosen independently from within the group comprising for example an acetyl or a tolyl group or a linear or cyclic alkyl group, with 1 to 10 atoms of carbon, non-substituted or substituted by one or more groups chosen independently from among —NO
2
, —OH, —COOH, —Cl, —NH
2
. For example, when R
1
and/or R
2
is a glucose unit, it can be ribose, deoxyribose, &bgr;-D-ribofuranosyl, etc.
When R
1
is a —NO
2
group, this group can be reduced to the c
Le Campion Laurence
Ouazzani Jamal
Burns Doane Swecker & Mathis L.L.P.
Centre National de la Recherche Scientifique
Marx Irene
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