EP2324030A1 - Explosive - Google Patents

Explosive

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Publication number
EP2324030A1
EP2324030A1 EP09777415A EP09777415A EP2324030A1 EP 2324030 A1 EP2324030 A1 EP 2324030A1 EP 09777415 A EP09777415 A EP 09777415A EP 09777415 A EP09777415 A EP 09777415A EP 2324030 A1 EP2324030 A1 EP 2324030A1
Authority
EP
European Patent Office
Prior art keywords
heptazine
explosive
trinitro
chemically active
active compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP09777415A
Other languages
German (de)
French (fr)
Inventor
Ulrich Baudis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Durferrit GmbH Thermotechnik
Original Assignee
Durferrit GmbH Thermotechnik
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Filing date
Publication date
Application filed by Durferrit GmbH Thermotechnik filed Critical Durferrit GmbH Thermotechnik
Publication of EP2324030A1 publication Critical patent/EP2324030A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00—Compositions containing a nitrated organic compound
    • C06B25/04—Compositions containing a nitrated organic compound the nitrated compound being an aromatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/16—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00—Compositions containing a nitrated organic compound
    • C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine

Definitions

  • the invention relates to an explosive.
  • nitro groups that is, NO 2 groups
  • TNT trinitrotoluene
  • HMX hexogen
  • nitro groups that is, NO 2 groups
  • RDX Octogen
  • a disadvantage of these explosives is that the explosives themselves are very toxic, for example, TNT can cause allergic reactions on skin contact and hexogan even has a carcinogenic effect.
  • the object of the invention is to provide a high-energy, easily handled explosive which can be used in many industrial applications.
  • the features of claim 1 are provided.
  • Advantageous uses, variants, embodiments and further developments of the invention are described in claims 2 to 7.
  • the explosive according to the invention contains as effective chemical compound fertil 2,6, 10-trinitro-s-heptazine and / or its derivatives.
  • the active chemical compound may generally form an explosive or a component of the explosive.
  • 2-amino-6,10-dinitro-s-heptazine or 2,6-diamino-10-nitro can be used as the chemically active compound.
  • s-heptazine that is derivatives of 2,6,10-trinitro-s-heptazine, be provided.
  • 2,6,10-trinitro-s-heptazine as a chemically active compound in the explosive of the invention is that it has a perfectly balanced oxygen-carbon balance.
  • 2,6,10-trinitro-s-heptazine whose molecular formula is C 6 Nio O 6 , decomposes quantitatively into carbon monoxide (CO) and nitrogen according to the relationship
  • 2,6,10-trinitro-s-heptazine a chemically active compound with high energy potential.
  • 2,6,10-trinitro-s-heptazine is a highly explosive which can be used in a wide range of applications, in particular as a propellant charge.
  • the explosive according to the invention consisting of the aforementioned chemically active compounds, as a gas generator be used.
  • gas generators are used for example in vehicle construction, for example for the production of airbags, belt tensioner systems and the like.
  • Another essential advantage of the invention is that for the preparation of 2,6,10-trinitro-s-heptazine and / or its derivatives 2-amino-6,10-dinitro-s-heptazine and 2,6-diamino-lO -nitro-s-heptazine chemically inert and toxicologically harmless substances can be used.
  • Triamino-s-heptazine known under the name Meiern
  • Meiern Triamino-tri-s-triazines, Cyamellurtriazide or 1, 3, 4, 6, 7, 9, 9b - Heptaazaphenalene-2,5,8-triamines.
  • Another possible starting material for the chemically active compound of the explosive according to the invention is the polymer of 2,6,10-triamino-s-heptazine, known under the name Melon.
  • Particularly suitable as starting material for the chemically active compound according to the invention is the regenerating agent for nitrocarburizing salt baths manufactured and sold under the brand name REG1® by HEF-Durferrit GmbH, Mannheim (DE), which contains a mixture of melon and Meiern.
  • Meiern, Melon and also of REG1® are chemically inert and non-toxic.
  • nitration is carried out for the preparation of 2,6,10-trinitro-s-heptazine or its derivatives Meiern, Melon or REG1® using suitable nitrating reagents.
  • REG1® being used as starting material, the nitration yields a mixture of 2,6,10-trinitro-s-heptazine, its derivatives and another chemically active compound, which are generally obtained by treating REGl ® with nitrating acid or nitrating reagents, and which is hereinafter called nitromelone.
  • This nitromelone as a novel chemically active compound can be used alone or in admixture with 2,6,10-trinitro-s-heptazine and its derivatives as a chemically active compound in the explosive of the invention.
  • nitromelone has largely properties that correspond to those of 2,6,10-trinitro-s-heptazine and its derivatives.
  • FIG. 1 Structural formula of trinitro-s-heptazine.
  • FIG. 2 Structural formula of triamino-s-heptazine.
  • FIG. 3 Structural formula of tripotassium cyamellurate.
  • FIG. 4 Structural formula of cyamelluric acid.
  • FIG. 5 Structural formula of trichloro-s-heptazine (trichlorocamellurate).
  • FIG. 6 Nitration of trichloro-s-heptazine.
  • FIG. 7 structural formula of melon.
  • FIG. 8 Structural formula of nitromelone.
  • FIG. 1 shows the structural formula of 2,6,10-trinitro-s-heptazine, which is used as a chemically active compound in the explosive according to the invention.
  • the derivatives of 2,6,10-trinitro-s-heptazine namely 2-amino-6,10-dinitro-s-heptazine and 2,6-diamino-10-nitro-s-heptazine, as chemically active compound of the explosive according to the invention can be used.
  • This chemically active compound forms an explosive with high energy potential and balanced oxygen-carbon balance, which convert completely in a blast of explosives in carbon monoxide and nitrogen.
  • the chemically active compound forms propellant and in particular gas generators that can be used for example for airbags.
  • the 2,6,10-trinitro-s-heptazine can be prepared by nitration of 2,6,10-trinitro-s-heptazine known as Meiern or triamino-tri-s-triazines.
  • Figure 2 shows the structural formula of Meiern.
  • the nitration of Meiern carried out using known nitration reactions, such as those described in Organikum, Wiley VCH, Weinheim 2001 (ISBN 3-527-29985-8), pages 188 ff and 358-361.
  • nitric acid or nitrating acid a mixture of nitric acid and sulfuric acid.
  • 2-amino-6,10-dinitro-s-heptazine and 2,6-diamino-10-nitro-s-heptazine are similarly preparable by incomplete or broken nitration.
  • Another possibility of synthesis consists in the diazotization and subsequent nitration of 2,6, 10-triamino-s-heptazine.
  • ReG1® is a mixture of melon, a polymer of triamino-s-heptazine of the formula [C 6 H 3 Ng] x and Meiern.
  • the structural formula of Melon is shown in FIG.
  • the chemically active compounds are prepared by nitration of REGl ®, where also the aforementioned nitration reactions can be used.
  • tripotassium cyanurate As an alternative starting material for the preparation of the 2,6,10-trinitro-s-heptazine according to the invention, tripotassium cyanurate (FIG. 3), the tri-potassium salt of cycamelluric acid or other alkali metal aziles of cyammelluric acid (FIG. 4), for example the sodium or lithium salt, may be used become.
  • Trikaliumcyamellurat has the gross formula K 3 C 6 N 7 O 3 .
  • Triphenyl cyanurate is obtained by cooking REG1® or melon in concentrated potash solution for 24 hours in very good yield. It contains crystallized, undried form of water of crystallization, which can be removed by heating in vacuo.
  • FIG. 8 shows the structural formula of a further chemically active compound, referred to below as nitromelone, which, as an alternative or in addition to the previously mentioned chemically active compounds, 2,6,10-trinitro-s-heptazine, 2-amino-6,10-dinitro- s-heptazine and 2,6-diamino-10-nitro-s-heptazine, in the explosive according to the invention can be used.
  • nitromelone 2,6,10-trinitro-s-heptazine, 2-amino-6,10-dinitro- s-heptazine and 2,6-diamino-10-nitro-s-heptazine, in the explosive according to the invention can be used.
  • nitromelone is chosen according to the name of nitrocellulose.
  • Nitromelone can be obtained by known nitration reactions by allowing nitrating acid or nitrating reagents, for example aceryl nitrate or - working safer - a mixture of acetic anhydride, in anhydrous acetic acid with the addition of concentrated nitric acid with good cooling to REG1® act.
  • nitrating acid or nitrating reagents for example aceryl nitrate or - working safer - a mixture of acetic anhydride
  • this mixture can be used as an explosive.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention relates to an explosive comprising 2,6,10-trinitro-s-heptazine and/or derivatives thereof as an active chemical compound.

Description

Sprengstoff explosive
Die Erfindung betrifft einen Sprengstoff.The invention relates to an explosive.
Bei bekannten modernen Sprengstoffen, wie beispielsweise Trinitrotoluol (TNT) oder Hexogen (HMX) werden zu deren Herstellung Nitrogruppen, das heißt NO2-Gruppen, in ein kohlenstoff- und stickstoffhaltiges organisches Molekül durch eine Nitrierungsreaktion eingebaut. Auf diese Weise wird der für die Verbrennung beziehungsweise für die explosionsartige Umsetzung des Sprengstoffs notwendige Sauerstoff in der wirksamen chemischen Verbindung des Sprengstoffs selbst verankert. Die sogenannten Sprengstoffe sind sehr energiereich und sind mit weiteren Sprengstoffen, wie zum Beispiel Octogen (RDX), in vielen Applikationen im industriellen Einsatz.In known modern explosives such as trinitrotoluene (TNT) or hexogen (HMX), nitro groups, that is, NO 2 groups, are incorporated into a carbon- and nitrogen-containing organic molecule by a nitration reaction to produce them. In this way, the necessary for the combustion or for the explosive reaction of the explosive oxygen in the effective chemical compound of the explosive itself is anchored. The so-called explosives are very energetic and are in many applications in industrial applications with other explosives, such as Octogen (RDX).
Ein Nachteil dieser Sprengstoffe besteht darin, dass die Sprengstoffe selbst sehr giftig sind, wobei beispielsweise TNT bei Hautkontakt allergische Reaktionen auslösen kann und Hexogan sogar eine karzinogene Wirkung hat.A disadvantage of these explosives is that the explosives themselves are very toxic, for example, TNT can cause allergic reactions on skin contact and hexogan even has a carcinogenic effect.
Zudem ist nachteilig, dass derartige Sprengstoffe, wie zum Beispiel TNT, keine ausgeglichene Sauerstoff-Kohlenstoff Bilanz aufweisen, und dass die Ausgangsstoffe zur Herstellung der Sprengstoffe gefährlich sind.In addition, it is disadvantageous that such explosives, such as TNT, have no balanced oxygen-carbon balance, and that the starting materials for the production of explosives are dangerous.
Der Erfindung liegt die Aufgabe zugrunde, einen hochenergetischen, leicht handhabbaren Sprengstoff bereitzustellen, der in vielen industriellen Applikati- onen einsetzbar ist. Zur Lösung dieser Aufgabe sind die Merkmale des Anspruchs 1 vorgesehen. Vorteilhafte Verwendungen, Varianten, Ausfuhrungsformen und Weiterbildungen der Erfindung sind in den Ansprüchen 2 bis 7 beschrieben.The object of the invention is to provide a high-energy, easily handled explosive which can be used in many industrial applications. To solve this problem, the features of claim 1 are provided. Advantageous uses, variants, embodiments and further developments of the invention are described in claims 2 to 7.
Der erfindungsgemäße Sprengstoff enthält als wirksame chemische Verbin- düng 2,6, 10-Trinitro-s-heptazin und/oder dessen Derivate.The explosive according to the invention contains as effective chemical compound fertil 2,6, 10-trinitro-s-heptazine and / or its derivatives.
Die wirksame chemische Verbindung kann generell einen Sprengstoff oder einen Bestandteil des Sprengstoffs bilden.The active chemical compound may generally form an explosive or a component of the explosive.
Dabei kann im erfindungsgemäßen Sprengstoff, alternativ oder zusätzlich zu 2,6,10-Trinitro-s-heptazin, als chemisch wirksame Verbindung 2-Amino-6,10- dinitro-s-heptazin oder 2,6-Diamino-lO-nitro-s-heptazin, das heißt Derivate von 2,6,10-Trinitro-s-heptazin, vorgesehen sein.In the explosive according to the invention, alternatively or in addition to 2,6,10-trinitro-s-heptazine, 2-amino-6,10-dinitro-s-heptazine or 2,6-diamino-10-nitro can be used as the chemically active compound. s-heptazine, that is derivatives of 2,6,10-trinitro-s-heptazine, be provided.
Ein wesentlicher Vorteil von 2,6,10-Trinitro-s-heptazin als chemisch wirksame Verbindung in dem erfindungsgemäßen Sprengstoff besteht darin, dass diese eine vollkommen ausgeglichene Sauerstoff-Kohlenstoff-Bilanz aufweist. Bei Initiierung eines Zerfalls des Sprengstoffs zersetzt sich 2,6,10-Trinitro-s- heptazin, dessen Summenformel C6 Nio O6 lautet, quantitativ in Kohlenmono- xid (CO) und Stickstoff gemäß der BeziehungA significant advantage of 2,6,10-trinitro-s-heptazine as a chemically active compound in the explosive of the invention is that it has a perfectly balanced oxygen-carbon balance. Upon initiation of disintegration of the explosive, 2,6,10-trinitro-s-heptazine, whose molecular formula is C 6 Nio O 6 , decomposes quantitatively into carbon monoxide (CO) and nitrogen according to the relationship
C6 N10 O6 → 6 CO + 5 N2 C 6 N 10 O 6 → 6 CO + 5 N 2
Diese komplette Zersetzung in thermodynamisch stabile Gase macht 2,6,10- Trinitro-s-heptazin zu einer chemisch wirksamen Verbindung mit hohem Energiepotential. Somit ist 2,6,10-Trinitro-s-heptazin, ebenso wie auch seine Derivate, ein hochexplosiver Sprengstoff, der in einem breiten Anwendungsfeld, insbesondere auch als Treibladung, einsetzbar ist.This complete decomposition into thermodynamically stable gases makes 2,6,10-trinitro-s-heptazine a chemically active compound with high energy potential. Thus 2,6,10-trinitro-s-heptazine, as well as its derivatives, is a highly explosive which can be used in a wide range of applications, in particular as a propellant charge.
Besonders vorteilhaft kann der erfindungsgemäße Sprengstoff, bestehend aus den vorgenannten chemisch wirksamen Verbindungen, auch als Gasgenerator eingesetzt werden. Derartige Gasgeneratoren werden beispielsweise im Fahrzeugbau, beispielsweise zur Herstellung von Airbags, Gurtstraffersystemen und dergleichen verwendet.Particularly advantageously, the explosive according to the invention, consisting of the aforementioned chemically active compounds, as a gas generator be used. Such gas generators are used for example in vehicle construction, for example for the production of airbags, belt tensioner systems and the like.
Derartige Einsatzfalle des erfiridungsgemäßen Sprengstoffs sind insbesondere auch deshalb möglich, da die chemisch wirksamen Verbindungen nicht giftig, gefahrlos und einfach handhabbar sind.Such use cases of the explosive according to the invention are also possible in particular because the chemically active compounds are not toxic, safe and easy to handle.
Ein weiterer wesentlicher Vorteil der Erfindung besteht darin, dass zur Herstellung von 2,6,10-Trinitro-s-heptazin und/oder seiner Derivate 2-Amino-6,10- dinitro-s-heptazin und 2,6-Diamino-lO-nitro-s-heptazin chemisch inerte und toxikologisch unbedenkliche Stoffe verwendet werden können.Another essential advantage of the invention is that for the preparation of 2,6,10-trinitro-s-heptazine and / or its derivatives 2-amino-6,10-dinitro-s-heptazine and 2,6-diamino-lO -nitro-s-heptazine chemically inert and toxicologically harmless substances can be used.
Als Ausgangsstoff für diese chemisch wirksame Verbindung kann einerseits Triamino-s-heptazin, bekannt unter dem Namen Meiern, verwendet werden. Andere Bezeichnungen für Meiern sind Triamino-tri-s-triazine, Cyamellurtria- mide oder 1, 3, 4, 6, 7, 9, 9b - Heptaazaphenalene-2,5,8-triamine.As a starting material for this chemically active compound on the one hand Triamino-s-heptazine, known under the name Meiern, can be used. Other names for Meiern are Triamino-tri-s-triazines, Cyamellurtriazide or 1, 3, 4, 6, 7, 9, 9b - Heptaazaphenalene-2,5,8-triamines.
Ein weiterer möglicher Ausgangsstoff für die chemisch wirksame Verbindung des erfindungsgemäßen Sprengstoffs ist das Polymerisat des 2,6,10-Triamino- s-heptazins, bekannt unter dem Namen Melon.Another possible starting material for the chemically active compound of the explosive according to the invention is the polymer of 2,6,10-triamino-s-heptazine, known under the name Melon.
Besonders vorteilhaft eignet sich als Ausgangsstoff für die erfindungsgemäße chemisch wirksame Verbindung das unter dem Markennamen REGl ® von der Firma HEF-Durferrit GmbH, Mannheim (DE) hergestellte und vertriebene Regenerierungsmittel für Nitrocarburiersalzbäder, welches ein Gemisch von Melon und Meiern enthält.Particularly suitable as starting material for the chemically active compound according to the invention is the regenerating agent for nitrocarburizing salt baths manufactured and sold under the brand name REG1® by HEF-Durferrit GmbH, Mannheim (DE), which contains a mixture of melon and Meiern.
Ein wesentlicher Vorteil von Meiern, Melon und auch von REG1® besteht darin, dass diese Stoffe chemisch inert und ungiftig sind. Generell wird zur Herstellung von 2,6,10-Trinitro-s-heptazin oder seiner Derivate Meiern, Melon oder REG1® unter Einsatz von geeigneten nitrierenden Reagenzien nitriert. Im Falle, dass REG1® als Ausgangsstoff verwendet wird, wird bei der Nitrierung eine Mischung von 2,6,10-Trinitro-s-heptazin, dessen Derivaten und einer weiteren chemisch wirksamen Verbindung erhalten, die sich generell bei Behandlung von REGl ® mit Nitriersäure oder nitrierenden Reagenzien ergibt, und welche im Folgenden Nitromelon genannt wird.An essential advantage of Meiern, Melon and also of REG1® is that these substances are chemically inert and non-toxic. In general, nitration is carried out for the preparation of 2,6,10-trinitro-s-heptazine or its derivatives Meiern, Melon or REG1® using suitable nitrating reagents. In the case of REG1® being used as starting material, the nitration yields a mixture of 2,6,10-trinitro-s-heptazine, its derivatives and another chemically active compound, which are generally obtained by treating REGl ® with nitrating acid or nitrating reagents, and which is hereinafter called nitromelone.
Dieses Nitromelon als neuartige chemisch wirksame Verbindung kann allein oder in Mischung mit 2,6,10-Trinitro-s-heptazin und dessen Derivaten als che- misch wirksame Verbindung in dem erfindungsgemäßen Sprengstoff eingesetzt werden.This nitromelone as a novel chemically active compound can be used alone or in admixture with 2,6,10-trinitro-s-heptazine and its derivatives as a chemically active compound in the explosive of the invention.
Dabei weist Nitromelon weitgehend Eigenschaften auf, die denen von 2,6,10- Trinitro-s-heptazin und seinen Derivaten entsprechen.In this case, nitromelone has largely properties that correspond to those of 2,6,10-trinitro-s-heptazine and its derivatives.
Die Erfindung wird im Folgenden anhand von Beispielen und Darstellungen erläutert. Dabei zeigen:The invention is explained below with reference to examples and illustrations. Showing:
Figur 1 : Strukturformel von Trinitro-s-heptazin.FIG. 1: Structural formula of trinitro-s-heptazine.
Figur 2: Strukturformel von Triamino-s-heptazin.FIG. 2: Structural formula of triamino-s-heptazine.
Figur 3: Strukturformel von Trikalium-Cyamellurat.FIG. 3: Structural formula of tripotassium cyamellurate.
Figur 4: Strukturformel von Cyamellursäure.FIG. 4: Structural formula of cyamelluric acid.
Figur 5: Strukturformel von Trichlor-s-heptazin (Trichlorcyamellurate).FIG. 5: Structural formula of trichloro-s-heptazine (trichlorocamellurate).
Figur 6: Nitrierung von Trichlor-s-heptazin.FIG. 6: Nitration of trichloro-s-heptazine.
Figur 7: Strukturformel von Melon. Figur 8: Strukturformel von Nitromelon.FIG. 7: structural formula of melon. FIG. 8: Structural formula of nitromelone.
Figur 1 zeigt die Strukturformel von 2,6,10-Trinitro-s-heptazin, welches als chemisch wirksame Verbindung im erfindungsgemäßen Sprengstoff zum Einsatz kommt. Alternativ oder zusätzlich können auch die Derivate von 2,6,10- Trinitro-s-heptazin, nämlich 2-Amino-6,10-dinitro-s-heptazin und 2,6- Diamino-10-nitro-s-heptazin, als chemisch wirksame Verbindung des erfindungsgemäßen Sprengstoffs eingesetzt werden.FIG. 1 shows the structural formula of 2,6,10-trinitro-s-heptazine, which is used as a chemically active compound in the explosive according to the invention. Alternatively or additionally, the derivatives of 2,6,10-trinitro-s-heptazine, namely 2-amino-6,10-dinitro-s-heptazine and 2,6-diamino-10-nitro-s-heptazine, as chemically active compound of the explosive according to the invention can be used.
Diese chemisch wirksame Verbindung bildet einen Sprengstoff mit hohem Energiepotential und ausgeglichener Sauerstoff-Kohlenstoffbilanz, wobei sich diese bei einer Explosion des Sprengstoffs vollständig in Kohlenmonoxid und Stickstoff umsetzen. Damit bildet die chemisch wirksame Verbindung Treibmittel und insbesondere Gasgeneratoren, die beispielsweise für Airbags eingesetzt werden können.This chemically active compound forms an explosive with high energy potential and balanced oxygen-carbon balance, which convert completely in a blast of explosives in carbon monoxide and nitrogen. Thus, the chemically active compound forms propellant and in particular gas generators that can be used for example for airbags.
Das 2,6,10-Trinitro-s-heptazin ist durch Nitrierung von 2,6,10-Trinitro-s- heptazin bekannt als Meiern oder Triamino-tri-s-triazine, herstellbar.The 2,6,10-trinitro-s-heptazine can be prepared by nitration of 2,6,10-trinitro-s-heptazine known as Meiern or triamino-tri-s-triazines.
Figur 2 zeigt die Strukturformel von Meiern. Die Nitrierung von Meiern erfolgt unter Anwendung bekannter Nitrierungsreaktionen, wie sie etwa beschrieben sind in Organikum, Wiley VCH, Weinheim 2001 (ISBN 3-527-29985-8), Seiten 188 ff und 358-361. In dieser Veröffentlichung werden als Substanzen, die das Nitrylkation NO2 + liefern, insbesondere Salpetersäure oder Nitriersäure (ein Gemisch aus Salpetersäure und Schwefelsäure) erwähnt. Die Substanzen 2- Amino-6, 10-dinitro-s-heptazin und 2,6-Diamino-lO-nitro-s-heptazin sind in ähnlicher Weise durch unvollständige beziehungsweise abgebrochene Nitrierung herstellbar. Eine andere Synthesemöglichkeit besteht in der Diazotierung und anschließenden Nitrierung des 2,6, 10-Triamino-s-heptazins.Figure 2 shows the structural formula of Meiern. The nitration of Meiern carried out using known nitration reactions, such as those described in Organikum, Wiley VCH, Weinheim 2001 (ISBN 3-527-29985-8), pages 188 ff and 358-361. In this publication, as substances providing the nitryl cation NO 2 + , mention is particularly made of nitric acid or nitrating acid (a mixture of nitric acid and sulfuric acid). The substances 2-amino-6,10-dinitro-s-heptazine and 2,6-diamino-10-nitro-s-heptazine are similarly preparable by incomplete or broken nitration. Another possibility of synthesis consists in the diazotization and subsequent nitration of 2,6, 10-triamino-s-heptazine.
Anstelle von Meiern, das in reiner Substanz nur schwer zugänglich ist (Juer- gens, Irran et al., J.Am.Chem.Soc.2003 125 (34) 10288-10300) kann als Aus- gangsstoff für die genannten chemisch wirksamen Verbindungen auch REG1®, ein organisches Regenerierungsmittel für Nitrocarburiersalzbäder der Firma HEF - Durferrit GmbH / Mannheim (DE), eingesetzt werden. REG1® ist ein Gemisch aus Melon, einem Polymerisat des Triamino-s-heptazins der Brutto- formel [C6H3Ng]x und Meiern.Instead of Meiern, which is only with difficulty accessible in pure substance (Juergens, Irran et al., J.Am.Chem.Soc.2003 125 (34) 10288-10300) can be indicated as Catalyst for the said chemically active compounds also REG1®, an organic regeneration agent for Nitrocarburiersalzbäder the company HEF - Durferrit GmbH / Mannheim (DE), are used. REG1® is a mixture of melon, a polymer of triamino-s-heptazine of the formula [C 6 H 3 Ng] x and Meiern.
Die Strukturformel von Melon ist in Figur 7 dargestellt. Die chemisch wirksamen Verbindungen werden durch Nitrierung von REGl ® hergestellt, wobei auch hier die vorgenannten Nitrierungsreaktionen zum Einsatz kommen können.The structural formula of Melon is shown in FIG. The chemically active compounds are prepared by nitration of REGl ®, where also the aforementioned nitration reactions can be used.
Als alternativer Ausgangsstoff zur Herstellung des erfindungsgemäßen 2,6,10- Trinitro-s-heptazins kann Trikaliumcyamellurat (Figur 3), das Tri-Kaliumsalz der Cyamellursäure oder andere Alkalisazle der Cyammellursäure (Figur 4), zum Beispiel das Natrium- oder Lithiumsalz, verwendet werden. Trikaliumcyamellurat hat die Bruttoformel K3C6N7O3. Man erhält Trikaliumcyamellurat durch 24 stündiges Kochen von REG1® oder von Melon in konzentrierter Kalilauge in sehr guter Ausbeute. Es enthält in kristallisierter, ungetrockneter Form Kristallwasser, das durch Erhitzen im Vakuum entfernt werden kann. Bei der Umsetzung von REG1® mit Alkalihydroxid werden die in REG1® enthaltenen C-NH-C beziehungsweise C-N-C-Brücken des Bestandteils Melon ge- spalten, das energiereiche s-Heptazin-System „C6N7" (alternative Bezeichnung: Tri-s-triazin-System oder Cyamellur-System) bleibt aber erhalten. Auf diese Weise kann man aus Melon eine relativ große Menge des energiereichen Tri-s-triazin-Systems in Form des Alkali-Salzes der Cyammelursäure gewinnen. Die Herstellung von K3C6N7O3 ist beschrieben bei: Kroke et al., New. J. Chem., 2002 (26) 508 - 512. Aus K3C6N7O3 kann dann das 2,6,10-Trinitro-s- heptazin durch folgende Nitrierungsreaktion hergestellt werden:As an alternative starting material for the preparation of the 2,6,10-trinitro-s-heptazine according to the invention, tripotassium cyanurate (FIG. 3), the tri-potassium salt of cycamelluric acid or other alkali metal aziles of cyammelluric acid (FIG. 4), for example the sodium or lithium salt, may be used become. Trikaliumcyamellurat has the gross formula K 3 C 6 N 7 O 3 . Triphenyl cyanurate is obtained by cooking REG1® or melon in concentrated potash solution for 24 hours in very good yield. It contains crystallized, undried form of water of crystallization, which can be removed by heating in vacuo. When reacting REG1® with alkali hydroxide, the C-NH-C or CNC bridges of the constituent melone contained in REG1® are split, the high-energy s-heptazine system "C6N7" (alternative designation: tri-s-triazine). In this way one can obtain from Melon a relatively large amount of the energetic tri-s-triazine system in form of the alkali salt of the Cyammelursäure.The production of K 3 C 6 N 7 O 3 is described in: Kroke et al., New J. Chem., 2002 (26) 508-512. The 2,6,10-trinitro-s-heptazine can then be prepared from K 3 C 6 N 7 O 3 by the following Nitriding reaction can be prepared:
C6N7(OK)3 + 6 HNO3 → C6N7(NOa)3 + 3 KNO3 + 3 H2O + 3/2 O2 Das erfindungsgemäße 2,6,10-Trinitro-s-heptazin kann auch aus dem Chlorid der Cyamellursäure synthesiert werden, indem die Chloratome durch Nitro- Gruppen substituiert werden (Figuren 5 und 6). Cyamellursäurechlorid (Trich- lor-tri-s-triazin) erhält man durch Umsetzung des Alkali-Salzes der Cyamellur- säure mit PC15. Die Herstellung von Cyamellursäurechlorid (C6N7Cl3) ist bei Kroke et al., New. J. Chem., 2002 (26) 508 - 512 beschrieben sowie in Schroeder und Kober, J. Org. Chem. 1962 (27) 4262-4266.C 6 N 7 (OK) 3 + 6 HNO 3 → C 6 N 7 (NOa) 3 + 3 KNO 3 + 3 H 2 O + 3/2 O 2 The 2,6,10-trinitro-s-heptazine according to the invention can also be synthesized from the chloride of cycamelluric acid by substituting the chlorine atoms by nitro groups (FIGS. 5 and 6). Cyamelluric acid chloride (trichloro-tri-s-triazine) is obtained by reacting the alkali salt of cycamelluric acid with PC15. The preparation of cycamelluric acid chloride (C 6 N 7 Cl 3 ) is described in Kroke et al., New. Chem., 2002 (26) 508-512 and in Schroeder and Kober, J. Org. Chem. 1962 (27) 4262-4266.
Weitere potentielle Ausgangsstoffe für die Herstellung von Trinitro-tri-s-triazin durch Nitrierung findet man bei Horvath-Bordon, Kroke et. al., Dalton Trans., 2004, 3900-3908.Further potential starting materials for the production of trinitro-tri-s-triazine by nitration can be found in Horvath-Bordon, Kroke et. al., Dalton Trans., 2004, 3900-3908.
Figur 8 zeigt die Strukturformel einer weiteren chemisch wirksamen Verbindung, im Folgenden Nitromelon genannt, welche alternativ oder zusätzlich zu den bisher genannten chemisch wirksamen Verbindungen, 2,6,10-Trinitro-s- heptazin, 2-Amino-6,10-dinitro-s-heptazin und 2,6-Diamino-10-nitro-s- heptazin, im erfindungsgemäßen Sprengstoff zum Einsatz kommen kann.FIG. 8 shows the structural formula of a further chemically active compound, referred to below as nitromelone, which, as an alternative or in addition to the previously mentioned chemically active compounds, 2,6,10-trinitro-s-heptazine, 2-amino-6,10-dinitro- s-heptazine and 2,6-diamino-10-nitro-s-heptazine, in the explosive according to the invention can be used.
Der Name Nitromelon ist in Anlehnung an die Bezeichnung von Nitrocellulose gewählt.The name nitromelone is chosen according to the name of nitrocellulose.
Nitromelon kann durch bekannte Nitrierungsreaktionen erhalten werden, indem man Nitriersäure oder nitrierende Reagenzien, zum Beispiel Acerylnitrat oder - arbeitstechnisch sicherer - ein Gemisch aus Essigsäureanhydrid, in wasserfreier Essigsäure unter Zusatz von konzentrierter Salpetersäure bei guter Kühlung auf REG1® einwirken lässt.Nitromelone can be obtained by known nitration reactions by allowing nitrating acid or nitrating reagents, for example aceryl nitrate or - working safer - a mixture of acetic anhydride, in anhydrous acetic acid with the addition of concentrated nitric acid with good cooling to REG1® act.
Je nach spezifischem Prozessablauf der Nitrierung von REGl ® wird ein Gemisch von Nitromelon und 2,6,10-Trinitro-s-heptazin und seinen Derivaten erhalten, wobei dieses Gemisch als Sprengstoff verwendet werden kann. Depending on the specific process of the nitration of REGl ®, a mixture of nitromelone and 2,6,10-trinitro-s-heptazine and its derivatives is obtained, this mixture can be used as an explosive.

Claims

Patentansprüche claims
1. Sprengstoff dadurch gekennzeichnet, dass dieser als wirksame chemische Verbindung 2,6,10-Trinitro-s-heptazin und/oder dessen Derivate enthält.1. explosive characterized in that it contains as an effective chemical compound 2,6,10-trinitro-s-heptazine and / or its derivatives.
2. Sprengstoff nach Anspruch 1, dadurch gekennzeichnet, dass dieser als chemisch wirksame Verbindung 2-Amino-6,10-dinitro-s-heptazin als Derivat von 2,6,10-Trinitro-s-heptazin enthält.2. explosive according to claim 1, characterized in that it contains as a chemically active compound 2-amino-6,10-dinitro-s-heptazine as a derivative of 2,6,10-trinitro-s-heptazine.
3. Sprengstoff nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet, dass dieser als chemisch wirksame Verbindung 2,6-Diamino-10-nitro-s- heptazin als Derivat von 2,6, 10-Trinitro-s-heptazin enthält.3. explosive according to one of claims 1 or 2, characterized in that it contains as a chemically active compound 2,6-diamino-10-nitro-s-heptazine as a derivative of 2,6, 10-trinitro-s-heptazine.
4. Sprengstoff nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass zusätzlich oder alternativ zu 2-Amino-6,10-dinitro-s-heptazin ein mit Nitriersäure oder nitrierenden Reagenzien behandeltes Melon als wirksame chemische Verbindung eingesetzt wird.4. explosive according to one of claims 1 to 3, characterized in that in addition to or as an alternative to 2-amino-6,10-dinitro-s-heptazine a treated with nitrating or nitrating reagents melon is used as an effective chemical compound.
5. Sprengstoff nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass dessen wirksame chemische Verbindungen erhältlich sind aus einem mit Nitriersäure oder nitrierenden Reagenzien behandelten REGl ®.5. Explosive agent according to one of claims 1 to 4, characterized in that the active chemical compounds are obtainable from a treated with nitrating acid or nitrating reagents REGI ®.
6. Verwendung des Sprengstoffs nach einem der Ansprüche 1 bis 5 als Treibmittel.6. Use of the explosive according to one of claims 1 to 5 as a blowing agent.
7. Verwendung des Sprengstoffs nach einem der Ansprüche 1 bis 5 als Gasgenerator. 7. Use of the explosive according to one of claims 1 to 5 as a gas generator.
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