EP0348797A2 - Application of a carbonyl group containing compound - Google Patents

Application of a carbonyl group containing compound Download PDF

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Publication number
EP0348797A2
EP0348797A2 EP89111201A EP89111201A EP0348797A2 EP 0348797 A2 EP0348797 A2 EP 0348797A2 EP 89111201 A EP89111201 A EP 89111201A EP 89111201 A EP89111201 A EP 89111201A EP 0348797 A2 EP0348797 A2 EP 0348797A2
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EP
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Prior art keywords
nitrate
carbonyl
oxidizing agent
containing oxidizing
explosives
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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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EP89111201A
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German (de)
French (fr)
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EP0348797A3 (en
Inventor
Claude Fürbringer
Horst Dr. Pauling
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F Hoffmann La Roche AG
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F Hoffmann La Roche AG
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Publication of EP0348797A2 publication Critical patent/EP0348797A2/en
Publication of EP0348797A3 publication Critical patent/EP0348797A3/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B33/00—Compositions containing particulate metal, alloy, boron, silicon, selenium or tellurium with at least one oxygen supplying material which is either a metal oxide or a salt, organic or inorganic, capable of yielding a metal oxide
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B31/00—Compositions containing an inorganic nitrogen-oxygen salt

Definitions

  • the present invention relates to the use of carbonyl compounds, namely 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid for the production of explosives (explosives, shooting or fuels and pyrotechnic substances), and a method for producing such explosives , and these explosives themselves.
  • explosives based on ascorbic acid or erythorbic acid are known, which are produced by heating ascorbic acid or erythorbic acid together with a nitrate-containing oxidizing agent or by heating one degradation product obtained from ascorbic acid or erythorbic acid mixed with a nitrate-containing oxidizing agent.
  • the present invention thus relates to a method for producing explosives, which consists in that 5,6-carbonyl-ascorbic acid or 5,6-carbonyl erythorbic acid mixed with a nitrate-containing oxidizing agent and optionally with other additives.
  • the 5,6-carbonyl-ascorbic acid and its production is from the Japanese patent publication 7031601 (13.10.1970), abstracted in C.A. 74 (1971) Ref. 88 266 C known.
  • the corresponding erythorbic acid derivative can be prepared analogously.
  • the nitrate-containing oxidizing agent used is preferably an alkali metal or alkaline earth metal nitrate, in particular potassium nitrate, or ammonium nitrate or a mixture of these nitrates.
  • the nitrate-containing oxidizing agent and the carbonyl compound are preferably used in a weight ratio of about 40:60 - 80:20, preferably about 60:40 - 65:35.
  • the explosives according to the invention are characterized in that they are a mixture of 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid and a nitrate-containing oxidizing agent, and if appropriate contain further additives.
  • the nitrate-containing oxidizing agent is preferably an alkali or alkaline earth metal nitrate, in particular potassium nitrate, or ammonium nitrate or a mixture of these nitrates.
  • Organic nitrates can be used as further nitrate-containing oxidizing agents.
  • An organic nitrate is to be understood here to mean any customary, carbon-containing nitrate with a stoichiometric excess of oxygen, which is usually used in the pyrotechnic industry or in the explosives industry.
  • suitable organic Nitrates are nitrocellulose, nitroglycerin or pentaerythritol tetranitrate.
  • the weight ratio between the nitrate-containing oxidizing agent (based on potassium nitrate) and the carbonyl compound is about 40: 60 - 80: 20, in particular about 60: 40 - 65: 35.
  • the mixture according to the invention can contain additives such as gelling agents or stabilizers, such as substituted ureas, e.g. Arkardit® or Centralit®; substituted urethanes, phthalates, polymers, additives to light sets such as sodium, barium, strontium or copper salts, as well as other additives, e.g. to increase the explosion energy or to improve other desirable properties such as boron or nitroguanidine.
  • additives such as gelling agents or stabilizers, such as substituted ureas, e.g. Arkardit® or Centralit®; substituted urethanes, phthalates, polymers, additives to light sets such as sodium, barium, strontium or copper salts, as well as other additives, e.g. to increase the
  • the explosive according to the invention can be used as an explosive, e.g. used in mining, as a gun or fuel or as a pyrotechnic material or as a high-energy mixture for various drive purposes.
  • This explosive can be used, for example, for the manufacture of cartridges or cartridges, for light or signal ammunition, for rockets, for shooting devices for technical purposes, and for fireworks or the like.
  • the explosive according to the invention is characterized by low corrosiveness, high driving force and low smoke development. Compared to similar known explosives, it has the following advantageous properties: higher explosive power, significantly lower hygroscopicity, better stability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Es wird die Verwendung von Carbonylverbindungen, nämlich von 5,6-Carbonyl-ascorbinsäure bzw. 5,6-Carbonyl-erythorbinsäure zur Herstellung von Explosivstoffen, sowie ein Verfahren zur Herstellung solcher Explosivstoffe, und diese Explosivstoffe selbst beschrieben.The use of carbonyl compounds, namely 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid for the production of explosives, as well as a process for the production of such explosives, and these explosives themselves are described.

Description

Die vorliegende Erfindung betrifft die Verwendung von Carbonylverbindungen, nämlich von 5,6-Carbonyl-ascorbinsäure bzw. 5,6-Carbonyl-erythorbinsäure zur Herstellung von Explosivstoffen (Sprengstoffen, Schiess- oder Treibstoffen und pyrotechnischen Stoffen), sowie ein Verfahren zur Her­stellung solcher Explosivstoffe, und diese Explosivstoffe selbst.The present invention relates to the use of carbonyl compounds, namely 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid for the production of explosives (explosives, shooting or fuels and pyrotechnic substances), and a method for producing such explosives , and these explosives themselves.

Aus der US Patentschrift Nr. 4,497,676 und der Europä­ischen Patentpublikation Nr. 268 996 sind Explosivstoffe auf Basis von Ascorbinsäure bzw. Erythorbinsäure bekannt geworden, welche hergestellt werden, indem man Ascorbinsäure oder Erythorbinsäure zusammen mit einem Nitrat-haltigen Oxidationsmittel erhitzt oder indem man ein durch Erhitzen von Ascorbinsäure bzw. Erythorbinsäure erhaltenes Abbauprodukt mit einem Nitrat-haltigen Oxidati­onsmittel vermischt.From US Pat. No. 4,497,676 and European Patent Publication No. 268 996, explosives based on ascorbic acid or erythorbic acid are known, which are produced by heating ascorbic acid or erythorbic acid together with a nitrate-containing oxidizing agent or by heating one degradation product obtained from ascorbic acid or erythorbic acid mixed with a nitrate-containing oxidizing agent.

Es wurde nun festgestellt, dass man ein qualitativ besseres Produkt dadurch erhalten kann, dass man anstelle von Ascorbinsäure bzw. Erythorbinsäure die entsprechenden 5,6-Carbonylderivate, also 5,6-Carbonyl-ascorbinsäure oder 5,6-Carbonyl-erythorbinsäure verwendet.It has now been found that a better quality product can be obtained by using the corresponding 5,6-carbonyl derivatives, i.e. 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid, instead of ascorbic acid or erythorbic acid.

Die vorliegende Erfindung bezieht sich somit auf ein Verfahren zur Herstellung von Explosivstoffen, welches darin besteht, dass man 5,6-Carbonyl-ascorbinsäure oder 5,6-Carbonyl-erythorbinsäure mit einem Nitrat-haltigen Oxidationsmittel und gegebenenfalls mit weiteren Zusätzen vermischt.The present invention thus relates to a method for producing explosives, which consists in that 5,6-carbonyl-ascorbic acid or 5,6-carbonyl erythorbic acid mixed with a nitrate-containing oxidizing agent and optionally with other additives.

Die 5,6-Carbonyl-ascorbinsäure und deren Herstellung ist aus der japanischen Patentpublikation 7031601 (13.10.1970), abstrahiert in C.A. 74 (1971) Ref. 88 266 C bekannt. Das entsprechende Erythorbinsäurederivat kann in Analogie hierzu hergestellt werden.The 5,6-carbonyl-ascorbic acid and its production is from the Japanese patent publication 7031601 (13.10.1970), abstracted in C.A. 74 (1971) Ref. 88 266 C known. The corresponding erythorbic acid derivative can be prepared analogously.

Als Nitrat-haltiges Oxidationsmittel verwendet man vorzugsweise ein Alkali- oder Erdalkalimetallnitrat, ins­besondere Kaliumnitrat, oder Ammoniumnitrat oder ein Ge­misch dieser Nitrate.The nitrate-containing oxidizing agent used is preferably an alkali metal or alkaline earth metal nitrate, in particular potassium nitrate, or ammonium nitrate or a mixture of these nitrates.

Vorzugsweise verwendet man das Nitrat-haltige Oxidati­onsmittel und die Carbonylverbindung in einem Gewichtsver­hältnis von etwa 40 : 60 - 80 : 20, vorzugsweise von etwa 60 : 40 - 65 : 35.The nitrate-containing oxidizing agent and the carbonyl compound are preferably used in a weight ratio of about 40:60 - 80:20, preferably about 60:40 - 65:35.

Die so erhaltenen erfindungsgemässen Explosivstoffe (Sprengstoffe, Schiess- oder Treibstoffe und pyrotechnische Stoffe) sind dadurch gekennzeichnet, dass sie ein Gemisch von 5,6-Carbonyl-ascorbinsäure bzw. 5,6-Carbonyl-­erythorbinsäure und einem Nitrat-haltigen Oxidationsmittel, und gegebenenfalls weitere Zusätze enthalten.The explosives according to the invention thus obtained (explosives, shooting or propellants and pyrotechnic substances) are characterized in that they are a mixture of 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid and a nitrate-containing oxidizing agent, and if appropriate contain further additives.

Das Nitrat-haltige Oxidationsmittel ist hierbei vor­zugsweise ein Alkali- oder Erdalkalimetallnitrat, insbe­sondere Kaliumnitrat, oder Ammoniumnitrat oder ein Gemisch dieser Nitrate. Als weitere Nitrat-haltige Oxidationsmittel können organische Nitrate verwendet werden. Unter einem organischen Nitrat ist hierbei jedes übliche, kohlenstoff-­haltige Nitrat mit einem stöchiometrischen Sauerstoffüberschuss zu verstehen, welches üblicherweise in der pyrotechnischen Industrie oder in der Sprengstoffindu­strie verwendet wird. Beispiele geeigneter organischer Nitrate sind Nitrocellulose, Nitroglycerin oder Pentaerithrit-Tetranitrat.The nitrate-containing oxidizing agent is preferably an alkali or alkaline earth metal nitrate, in particular potassium nitrate, or ammonium nitrate or a mixture of these nitrates. Organic nitrates can be used as further nitrate-containing oxidizing agents. An organic nitrate is to be understood here to mean any customary, carbon-containing nitrate with a stoichiometric excess of oxygen, which is usually used in the pyrotechnic industry or in the explosives industry. Examples of suitable organic Nitrates are nitrocellulose, nitroglycerin or pentaerythritol tetranitrate.

Gemäss einer bevorzugten Ausführungsform beträgt das Gewichtsverhältnis zwischen Nitrat-haltigem Oxidationsmit­tel (bezogen auf Kaliumnitrat) und der Carbonylverbindung etwa 40 : 60 - 80 : 20, insbesondere etwa 60 : 40 - 65 : 35. Das erfindungsgemässe Gemisch kann Zusatzstoffe wie Gelierungsmittel oder Stabilisatoren, wie substituierte Harnstoffe, z.B. Arkardit® oder Centralit®; substituierte Urethane, Phthalate, Polymere, Zusätze zu Leuchtsätzen, wie Natrium-, Barium-, Strontium- oder Kupfersalze, sowie an­dere Additive, z.B. zur Erhöhung der Explosionsenergie oder zur Verbesserung anderer wünschenswerter Eigenschaften, wie beispielsweise Bor oder Nitroguanidin, enthalten.According to a preferred embodiment, the weight ratio between the nitrate-containing oxidizing agent (based on potassium nitrate) and the carbonyl compound is about 40: 60 - 80: 20, in particular about 60: 40 - 65: 35. The mixture according to the invention can contain additives such as gelling agents or stabilizers, such as substituted ureas, e.g. Arkardit® or Centralit®; substituted urethanes, phthalates, polymers, additives to light sets such as sodium, barium, strontium or copper salts, as well as other additives, e.g. to increase the explosion energy or to improve other desirable properties such as boron or nitroguanidine.

Der erfindungsgemässe Explosivstoff kann als Spreng­stoff, z.B. im Bergbau, als Schiessstoff oder Treibstoff oder als pyrotechnisches Material oder als energiereiches Gemisch für verschiedene Antriebszwecke verwendet werden. Dieser Explosivstoff ist beispielsweise für die Herstellung von Patronen oder Kartuschen, für Leucht- oder Signalmuni­tion, für Raketen, für Schussapparate zu technischen Zwek­ken, sowie für Feuerwerkskörper oder dergleichen verwend­bar.The explosive according to the invention can be used as an explosive, e.g. used in mining, as a gun or fuel or as a pyrotechnic material or as a high-energy mixture for various drive purposes. This explosive can be used, for example, for the manufacture of cartridges or cartridges, for light or signal ammunition, for rockets, for shooting devices for technical purposes, and for fireworks or the like.

Der erfindungsgemässe Explosivstoff zeichnet sich durch geringe Korrosivität, hohe Treibkraft und geringe Rauch­entwicklung aus. Im Vergleich zu ähnlichen bekannten Ex­plosivstoffen besitzt er insbesondere die folgenden vor­teilhaften Eigenschaften: höhere Explosivkraft, deutlich geringere Hygroskopizität, bessere Stabilität.The explosive according to the invention is characterized by low corrosiveness, high driving force and low smoke development. Compared to similar known explosives, it has the following advantageous properties: higher explosive power, significantly lower hygroscopicity, better stability.

Beispielexample

In einem Rundkolben werden 74,4 g Kaliumnitrat und 44,75 g 5,6-Carbonyl-ascorbinsäure in 372 ml Wasser gelöst und anschliessend mit 22,4 ml 1N wässeriger Kaliumhy­droxydlösung versetzt. Die Lösung wird nun zuerst am Was­serstrahlvakuum, später am Hochvakuum zur Trockene einge­dampft. Das erhaltene weisse Gemisch wird in der Reibschale pulverisiert und anschliessend während mindestens 20 Stun­den bei 40oC im Vakuumtrockenschrank über Silikagel ge­trocknet. Man erhält 120 g eines Explosivstoffes mit einer Explosionswärme von 769 cal/g. Der Schmelzpunkt dieser Substanz ist nicht bestimmbar, sie beginnt bei etwa 200oC zu schäumen. pH einer Lösung von 1 g in 20 ml Wasser = 2,75. Wasserlöslichkeit: etwa 67 g/100 ml (25oC).74.4 g of potassium nitrate and 44.75 g of 5,6-carbonyl-ascorbic acid are dissolved in 372 ml of water in a round-bottomed flask, and 22.4 ml of 1N aqueous potassium hydroxide solution are then added. The solution is then evaporated to dryness first in a water jet vacuum and later in a high vacuum. The white mixture obtained is pulverized in the grater and then dried over silica gel in a vacuum drying cabinet at 40 ° C. for at least 20 hours. 120 g of an explosive with an explosion heat of 769 cal / g are obtained. The melting point of this substance cannot be determined, it begins to foam at around 200 o C. pH of a solution of 1 g in 20 ml of water = 2.75. Water solubility: about 67 g / 100 ml (25 o C).

Claims (7)

1. Explosivstoff, dadurch gekennzeichnet, dass er ein Gemisch von 5,6-Carbonyl-ascorbinsäure oder 5,6-Carbonyl-­erythorbinsäure und einem Nitrat-haltigen Oxidationsmittel, und gegebenenfalls weitere Zusätze enthält.1. explosive, characterized in that it contains a mixture of 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid and a nitrate-containing oxidizing agent, and optionally further additives. 2. Explosivstoff nach Anspruch 1, dadurch gekennzeich­net, dass das Nitrat-haltige Oxidationsmittel ein Alkali- oder Erdalkalimetallnitrat, insbesondere Kaliumnitrat, oder Ammoniumnitrat, oder ein Gemisch dieser Nitrate ist.2. Explosive according to claim 1, characterized in that the nitrate-containing oxidizing agent is an alkali or alkaline earth metal nitrate, in particular potassium nitrate, or ammonium nitrate, or a mixture of these nitrates. 3. Explosivstoff nach Anspruch 1 oder 2, dadurch ge­kennzeichnet, dass das Gewichtsverhältnis Nitrat-haltiges Oxidationsmittel: Carbonylverbindung zwischen 40 : 60 und 80 : 20, vorzugsweise zwischen 60 : 40 und 65 : 35 liegt.3. Explosive according to claim 1 or 2, characterized in that the weight ratio of nitrate-containing oxidizing agent: carbonyl compound is between 40:60 and 80:20, preferably between 60:40 and 65:35. 4. Verfahren zur Herstellung eines Explosivstoffes nach Anspruch 1, 2 oder 3, dadurch gekennzeichnet, dass man 5,6-Carbonyl-ascorbinsäure oder 5,6-Carbonyl-­erythorbinsäure mit einem Nitrat-haltigen Oxidationsmittel und gegebenenfalls mit Zusatzstoffen vermischt.4. A method for producing an explosive according to claim 1, 2 or 3, characterized in that 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid is mixed with a nitrate-containing oxidizing agent and optionally with additives. 5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, dass man als Nitrat-haltiges Oxidationsmittel ein Alkali- oder Erdalkalimetallnitrat, insbesondere Kaliumnitrat, oder Ammoniumnitrat, oder ein Gemisch dieser Nitrate verwendet.5. The method according to claim 4, characterized in that an alkali or alkaline earth metal nitrate, in particular potassium nitrate, or ammonium nitrate, or a mixture of these nitrates is used as the nitrate-containing oxidizing agent. 6. Verfahren nach Anspruch 4 oder 5, dadurch gekenn­zeichnet, dass man das Nitrat-haltige Oxidationsmittel und die Carbonylverbindung in einem Gewichtsverhältnis von etwa 40 : 60 bis 80 : 20, vorzugsweise von etwa 60 : 40 bis 65 : 35 verwendet.6. The method according to claim 4 or 5, characterized in that one uses the nitrate-containing oxidizing agent and the carbonyl compound in a weight ratio of about 40:60 to 80:20, preferably from about 60:40 to 65:35. 7. Verwendung von 5,6-Carbonyl-ascorbinsäure bzw. 5,6-Carbonyl-erythorbinsäure zur Herstellung von Explo­sivstoffen.7. Use of 5,6-carbonyl-ascorbic acid or 5,6-carbonyl-erythorbic acid for the production of explosives.
EP89111201A 1988-06-30 1989-06-20 Application of a carbonyl group containing compound Withdrawn EP0348797A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH249688 1988-06-30
CH2496/88 1988-06-30

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EP0348797A2 true EP0348797A2 (en) 1990-01-03
EP0348797A3 EP0348797A3 (en) 1990-05-23

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US (1) US4881993A (en)
EP (1) EP0348797A3 (en)
JP (1) JPH0248489A (en)
KR (1) KR910000579A (en)
AU (1) AU608452B2 (en)
DK (1) DK319089A (en)
NO (1) NO169535C (en)
ZA (1) ZA894799B (en)

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Publication number Priority date Publication date Assignee Title
US5486247A (en) * 1992-02-06 1996-01-23 Engsbraten; Bjoern Explosive composition, manufacture and use thereof
US5569875A (en) * 1992-03-16 1996-10-29 Legend Products Corporation Methods of making explosive compositions, and the resulting products
US5449423A (en) * 1992-10-13 1995-09-12 Cioffe; Anthony Propellant and explosive composition
US6599379B2 (en) * 2001-04-12 2003-07-29 Dmd Systems, Llc Low-smoke nitroguanidine and nitrocellulose based pyrotechnic compositions
US20040016482A1 (en) * 2001-11-19 2004-01-29 Fey Warren O Fuel for energetic compositions comprising caramel color bodies
US7344610B2 (en) 2003-01-28 2008-03-18 Hodgdon Powder Company, Inc. Sulfur-free propellant compositions

Citations (3)

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GB1601392A (en) * 1978-04-12 1981-10-28 Pyrodex Corp Gas generating compositions
US4497676A (en) * 1982-11-01 1985-02-05 Kurtz Earl F Gunpowder substituted composition and method
EP0268996A2 (en) * 1986-11-27 1988-06-01 F. Hoffmann-La Roche Ag Lactonic degradation product, process for its preparation and its use

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Publication number Priority date Publication date Assignee Title
US4728376A (en) * 1982-11-01 1988-03-01 Golden Power Of Texas, Inc. Explosive composition and method

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1601392A (en) * 1978-04-12 1981-10-28 Pyrodex Corp Gas generating compositions
US4497676A (en) * 1982-11-01 1985-02-05 Kurtz Earl F Gunpowder substituted composition and method
EP0268996A2 (en) * 1986-11-27 1988-06-01 F. Hoffmann-La Roche Ag Lactonic degradation product, process for its preparation and its use

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 74, Nr. 17, 26. April 1971, Seite 465, Zusammenfassung Nr. 88266c, Columbus, Ohio, US; & JP-B-45 031661 (YAMANOUCHI PHARMACEUTICAL CO., LTD) 13-10-1970 *

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AU608452B2 (en) 1991-03-28
JPH0248489A (en) 1990-02-19
NO892718D0 (en) 1989-06-29
EP0348797A3 (en) 1990-05-23
NO892718L (en) 1990-01-02
AU3703489A (en) 1990-01-04
US4881993A (en) 1989-11-21
DK319089A (en) 1989-12-31
DK319089D0 (en) 1989-06-27
ZA894799B (en) 1990-03-28
KR910000579A (en) 1991-01-29
NO169535C (en) 1992-07-08
NO169535B (en) 1992-03-30

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