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WO1999021795A1 - Method of producing adn prills - Google Patents

Method of producing adn prills Download PDF

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Publication number
WO1999021795A1
WO1999021795A1 PCT/SE1998/001938 SE9801938W WO9921795A1 WO 1999021795 A1 WO1999021795 A1 WO 1999021795A1 SE 9801938 W SE9801938 W SE 9801938W WO 9921795 A1 WO9921795 A1 WO 9921795A1
Authority
WO
WIPO (PCT)
Prior art keywords
medium
prills
adn
nonpolar
nena
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.)
Ceased
Application number
PCT/SE1998/001938
Other languages
French (fr)
Inventor
Abraham Langlet
Martin Johansson
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.)
Forsvarets Forskningsanstalt
Forsvarets Forskningsanstalt (FOA)
Original Assignee
Forsvarets Forskningsanstalt
Forsvarets Forskningsanstalt (FOA)
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Forsvarets Forskningsanstalt, Forsvarets Forskningsanstalt (FOA) filed Critical Forsvarets Forskningsanstalt
Priority to AU97717/98A priority Critical patent/AU9771798A/en
Publication of WO1999021795A1 publication Critical patent/WO1999021795A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B21/00—Nitrogen; Compounds thereof
    • C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
    • C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B21/00—Apparatus or methods for working-up explosives, e.g. forming, cutting, drying
    • C06B21/0033—Shaping the mixture
    • C06B21/005—By a process involving melting at least part of the ingredients
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B21/00—Apparatus or methods for working-up explosives, e.g. forming, cutting, drying
    • C06B21/0033—Shaping the mixture
    • C06B21/0066—Shaping the mixture by granulation, e.g. flaking
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/32—Compounds containing nitrogen bound to oxygen

Definitions

  • the method relates to a method of producing particles, prills, of ADN. More specifically, the invention concerns a method of producing in liquid phase ADN prills, in particular small prills, and a polymodal mixture containing such small ADN prills.
  • Ammonium dinitramide is an energetic oxidiser which can be used in many applications.
  • One application is that as oxidiser in rocket propellants, which is disclosed in e.g. US 5,498,303.
  • Advantages of using ADN in composite propellants instead of ammonium nitrate are described in, for instance, US 5,498,303 and WO 97/06099.
  • ADN When producing ADN, the product is obtained in the form of crystal aggregates which are not very suited to be directly mixed with a polymer system for producing a composite propellant. It is therefore desirable to produce prills of ADN. Prills allow a simpler handling system and result in a better rheology in mixing with polymer systems. Provided that suitable particle sizes can be produced, prills also enable easy production of polymodal mixtures.
  • a polymodal mixture consists of a plurality of different particle sizes which are so related to each other as to achieve a high packing density.
  • prills in liquid phase are previously known.
  • the substance is molten and dispersed to droplets in a liquid phase which is inert in relation to the substance.
  • the liquid phase is cooled to solidify the droplets into prills, and these are separated from the liquid phase.
  • Such a method for prilling of ADN is mentioned in Challenges in Propellants and Combustion - 100 Years after Nobel (Conference Proceedings, 1996, pp 627-635); May Lee Chan et al: ADN Propellant Technology.
  • a problem is that the particles must be washed clean with an organic solvent before they can be used in the production of propellants.
  • An object of the present invention is to provide an improved method of producing ADN prills in liquid phase.
  • a prilling method which allows production of small
  • ADN prills has been accomplished.
  • ADN prills with a diameter of less than 40 ⁇ m can be produced, which in turn allows the production of suitable polymodal mixtures for ADN-based propellants and explosives.
  • the inventive method comprises melting and dispersion of ADN in a nonpolar medium to obtain droplets of ADN in the medium; cooling of the medium for solidifying the droplets into prills and separation of said prills from the medium.
  • the invention is characterised by supplying ultrasonic energy to the medium during said dispersion.
  • the prilling can be carried out in a batch reactor and the ultrasonic energy can be supplied by means of an ultrasonic transducer immersed in the medium in the reactor.
  • the dispersion can be carried out by means of ultrasonic waves only, or ultra- sonic waves in combination with mechanical stirring.
  • the mixture of molten ADN in the nonpolar medium can be passed through a flow mixer to which ultrasonic energy is supplied.
  • a small amount of surfactant can advantageously be added to the nonpolar medium.
  • the surfactant makes the prills have a smooth and nice surface.
  • the added amount is normally smaller than 5% by weight based on the nonpolar medium.
  • Suitable surfactants are, for instance, laurylium sulphate, stearyl alcohol, sodium stearate, octylamine and dodecylamine.
  • the nonpolar medium consists essentially of a plasticiser, in which case a plasticiser which is normally used in polymer systems in the production of composite propellants and plastic-bonded explosives is selected.
  • Suitable plasticisers are DOS, DOA, vacuum oil, transformer oil, K-10, BTTN, M/E- NENA, TMETN, Me-NENA, Et-NENA, WM3, FEFO, BDNPF/A, DANPE, DINA, and GAPA. K-10 up to and including GAPA are all energetic plasticisers.
  • the nonpolar medium may contain a polymer for adjust- ing the viscosity of the medium.
  • the polymer can be, for instance, HTPB or some other polymer that is used in composite propellants or plastic-bonded explosives.
  • a suitable viscosity of the nonpolar medium is 10-250 mPas.
  • the supply of ultrasonic waves gives an intense dispersion of molten ADN in the medium, and very small prills with a diameter of less than 40 ⁇ m can be produced. This enables in turn the production of suitable polymodal mixtures for dense ADN- based propellants and explosives.
  • a suitable bimodal mixture of ADN prills may comprise, for instance, a first size fraction having a particle size greater than 80 ⁇ m, and a second size fraction having a particle size of less than 40 ⁇ m.
  • the ratio of the particle size in the first size fraction to the particle size in the second size fraction can be, for instance, about 5:1.
  • the weight ratio of the first to the second size fraction is suitably about 5:1.
  • the supply of ultrasonic energy can be combined with a low pressure/vacuum in the reactor when great demands are placed on the homogeneity of the prills.
  • the supply of ultrasonic waves also contributes to aerating the medium. For many applications, an acceptable homogeneity is therefore achieved by using the ultrasonic process without at the same time a low pressure being applied.
  • Prilling was carried out in a 1 -litre stainless steel batch reactor consisting of a cylindrical container with a tight cover.
  • the container was provided with a magnetic agitator and enclosed by a jacket to be passed by a heating medium and a cooling medium, respectively.
  • An ultrasonic transducer was arranged through the cover and immersed in the medium in the reactor.
  • the reactor was charged with 5 g of ADN, 700 ml of plasticiser (DOS, dioctyl sebacate) as a nonpolar medium and 200 mg of surfactant (laurylium sulphate).
  • DOS dioctyl sebacate
  • surfactant laaurylium sulphate
  • the mixture was heated to 96°C and kept at this temperature for 5 min during stirring by means of the magnetic agitator.
  • the ultrasonic transducer was operated at its maximum for 3 min and was then shut off and the mixture was quickly cooled to 20°C.
  • the resulting prills were filtered off from the plasticiser. Prills having a particle size of less than 40 ⁇ m were produced.
  • prills with a larger particle size could be prepared by lowering the intensity of the ultrasonic treatment.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Peptides Or Proteins (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)

Abstract

The invention relates to a method of producing prills of ADN. The method comprises melting and dispersion of ADN in a nonpolar medium to obtain droplets of ADN in the medium; cooling the medium for solidification of the droplets into prills and separation of said prills from the medium. The invention is characterised in that ultrasonic energy is supplied to the medium during dispersion. The invention also concerns a polymodal mixture of ADN prills containing prills having a particle size of less than 40 mu m produced according to the method.

Description

Method of Producing ADN Prills
The method relates to a method of producing particles, prills, of ADN. More specifically, the invention concerns a method of producing in liquid phase ADN prills, in particular small prills, and a polymodal mixture containing such small ADN prills.
Ammonium dinitramide is an energetic oxidiser which can be used in many applications. One application is that as oxidiser in rocket propellants, which is disclosed in e.g. US 5,498,303. Advantages of using ADN in composite propellants instead of ammonium nitrate are described in, for instance, US 5,498,303 and WO 97/06099.
When producing ADN, the product is obtained in the form of crystal aggregates which are not very suited to be directly mixed with a polymer system for producing a composite propellant. It is therefore desirable to produce prills of ADN. Prills allow a simpler handling system and result in a better rheology in mixing with polymer systems. Provided that suitable particle sizes can be produced, prills also enable easy production of polymodal mixtures. A polymodal mixture consists of a plurality of different particle sizes which are so related to each other as to achieve a high packing density.
The production of prills in liquid phase is previously known. The substance is molten and dispersed to droplets in a liquid phase which is inert in relation to the substance. The liquid phase is cooled to solidify the droplets into prills, and these are separated from the liquid phase. Such a method for prilling of ADN is mentioned in Challenges in Propellants and Combustion - 100 Years after Nobel (Conference Proceedings, 1996, pp 627-635); May Lee Chan et al: ADN Propellant Technology. A problem, however, is that the particles must be washed clean with an organic solvent before they can be used in the production of propellants.
By using the prior-art methods it is difficult to produce really small particles, i.e. with a diameter of less than 40 μm. For the production of compact ADN-based explosives it is, however, desirable to have such small particles.
An object of the present invention is to provide an improved method of producing ADN prills in liquid phase. A prilling method which allows production of small
ADN prills has been accomplished. ADN prills with a diameter of less than 40 μm can be produced, which in turn allows the production of suitable polymodal mixtures for ADN-based propellants and explosives.
The invention is defined in the appended claims.
The inventive method comprises melting and dispersion of ADN in a nonpolar medium to obtain droplets of ADN in the medium; cooling of the medium for solidifying the droplets into prills and separation of said prills from the medium. The invention is characterised by supplying ultrasonic energy to the medium during said dispersion.
The prilling can be carried out in a batch reactor and the ultrasonic energy can be supplied by means of an ultrasonic transducer immersed in the medium in the reactor. The dispersion can be carried out by means of ultrasonic waves only, or ultra- sonic waves in combination with mechanical stirring. Alternatively, the mixture of molten ADN in the nonpolar medium can be passed through a flow mixer to which ultrasonic energy is supplied.
A small amount of surfactant can advantageously be added to the nonpolar medium. The surfactant makes the prills have a smooth and nice surface. The added amount is normally smaller than 5% by weight based on the nonpolar medium. Suitable surfactants are, for instance, laurylium sulphate, stearyl alcohol, sodium stearate, octylamine and dodecylamine.
According to a preferred embodiment, the nonpolar medium consists essentially of a plasticiser, in which case a plasticiser which is normally used in polymer systems in the production of composite propellants and plastic-bonded explosives is selected.
Suitable plasticisers are DOS, DOA, vacuum oil, transformer oil, K-10, BTTN, M/E- NENA, TMETN, Me-NENA, Et-NENA, WM3, FEFO, BDNPF/A, DANPE, DINA, and GAPA. K-10 up to and including GAPA are all energetic plasticisers.
In addition to a plasticiser, the nonpolar medium may contain a polymer for adjust- ing the viscosity of the medium. The polymer can be, for instance, HTPB or some other polymer that is used in composite propellants or plastic-bonded explosives. A suitable viscosity of the nonpolar medium is 10-250 mPas. By using a plasticiser as a nonpolar medium, the prills can be directly mixed with a polymer system when producing composite propellants and plastic-bonded explosives without the particles first needing to be washed. The plasticiser and, where appropriate, the viscosity-controlling polymer are selected in consideration of the polymer system with which the prills are to be mixed. The plasticiser also protects the particles from the humidity of the air.
The supply of ultrasonic waves gives an intense dispersion of molten ADN in the medium, and very small prills with a diameter of less than 40 μm can be produced. This enables in turn the production of suitable polymodal mixtures for dense ADN- based propellants and explosives.
A suitable bimodal mixture of ADN prills may comprise, for instance, a first size fraction having a particle size greater than 80 μm, and a second size fraction having a particle size of less than 40 μm. The ratio of the particle size in the first size fraction to the particle size in the second size fraction can be, for instance, about 5:1. Also the weight ratio of the first to the second size fraction is suitably about 5:1.
The supply of ultrasonic energy can be combined with a low pressure/vacuum in the reactor when great demands are placed on the homogeneity of the prills. The supply of ultrasonic waves also contributes to aerating the medium. For many applications, an acceptable homogeneity is therefore achieved by using the ultrasonic process without at the same time a low pressure being applied.
The invention will now be described by means of Examples.
Example 1
Prilling was carried out in a 1 -litre stainless steel batch reactor consisting of a cylindrical container with a tight cover. The container was provided with a magnetic agitator and enclosed by a jacket to be passed by a heating medium and a cooling medium, respectively. An ultrasonic transducer was arranged through the cover and immersed in the medium in the reactor.
The reactor was charged with 5 g of ADN, 700 ml of plasticiser (DOS, dioctyl sebacate) as a nonpolar medium and 200 mg of surfactant (laurylium sulphate). The mixture was heated to 96°C and kept at this temperature for 5 min during stirring by means of the magnetic agitator. The ultrasonic transducer was operated at its maximum for 3 min and was then shut off and the mixture was quickly cooled to 20°C. The resulting prills were filtered off from the plasticiser. Prills having a particle size of less than 40 μm were produced.
Also prills with a larger particle size could be prepared by lowering the intensity of the ultrasonic treatment.
Repeated experiments were made with other plasticisers as a nonpolar medium, DOA, vacuum oil, transformer oil, K-10, BTTN, M/E-NENA, TMETN, Me-NENA, Et- NENA, WM3, FEFO, BDNPF/A, DANPE, DINA and GAPA being tested.

Claims

Claims:
1. A method of producing prills of ADN, comprising melting and dispersion of ADN in a nonpolar medium to obtain droplets of ADN in the medium; cooling of the medium for solidification of the droplets into prills and separation of said prills from the medium, characterised in that ultrasonic energy is supplied to the medium during dispersion.
2. A method as claimed in claim 1 , characterised in that prills having a particle size of less than 40 μm are produced.
3. A method as claimed in claim 1 , characterised in that said supply of ultrasonic energy is carried out by means of an ultrasonic transducer immersed in the medium.
4. A method as claimed in claim 1 , characterised in that a surfactant is added to the nonpolar medium.
5. A method as claimed in claim 1 , characterised in that the nonpolar medium essentially consists of a plasticiser.
6. A method as claimed in claim 5, characterised in that the plasticiser is selected from the group consisting of DOS, DOA, vacuum oil, transformer oil, K-10, BTTN, M/E-NENA, TMETN, Me-NENA, Et-NENA, WM3, FEFO, BDNPF/A, DANPE, DINA and GAPA.
7. A method as claimed in claim 5, characterised in that the nonpolar medium contains a polymer for adjusting the viscosity of the medium.
8. A method as claimed in claim 7, characterised in that the nonpolar medium has a viscosity of 10-250 mPas.
9. A polymodal mixture of ADN prills comprising prills with a particle size of less than 40 μm produced according to claim 1.
PCT/SE1998/001938 1997-10-28 1998-10-27 Method of producing adn prills Ceased WO1999021795A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU97717/98A AU9771798A (en) 1997-10-28 1998-10-27 Method of producing adn prills

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9703928-3 1997-10-28
SE9703928A SE512396C2 (en) 1997-10-28 1997-10-28 Methods of Preparing Prills of Ammonium Dinitramide (ADN)

Publications (1)

Publication Number Publication Date
WO1999021795A1 true WO1999021795A1 (en) 1999-05-06

Family

ID=20408770

Family Applications (3)

Application Number Title Priority Date Filing Date
PCT/SE1998/001938 Ceased WO1999021795A1 (en) 1997-10-28 1998-10-27 Method of producing adn prills
PCT/SE1998/001936 Ceased WO1999021793A1 (en) 1997-10-28 1998-10-27 Method of producing prills of ammonium dinitramide (adn)
PCT/SE1998/001937 Ceased WO1999021794A1 (en) 1997-10-28 1998-10-27 Method of producing adn prills suitable for use in a polymer system

Family Applications After (2)

Application Number Title Priority Date Filing Date
PCT/SE1998/001936 Ceased WO1999021793A1 (en) 1997-10-28 1998-10-27 Method of producing prills of ammonium dinitramide (adn)
PCT/SE1998/001937 Ceased WO1999021794A1 (en) 1997-10-28 1998-10-27 Method of producing adn prills suitable for use in a polymer system

Country Status (3)

Country Link
AU (3) AU9771798A (en)
SE (1) SE512396C2 (en)
WO (3) WO1999021795A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013043099A3 (en) * 2011-09-22 2013-06-20 Monogel Ab Process for manufacturing particles and particles thereby manufactured

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6610157B1 (en) 2000-01-14 2003-08-26 Alliant Techsystems Inc. Prilled energetic particles, and process for making the same
FR2935969B1 (en) 2008-09-18 2011-05-13 Snpe Materiaux Energetiques PROCESS FOR OBTAINING DNA CRYSTALS BY VISCOUS-BASED CRYSTALLIZATION; DNA CRYSTALS AND ENERGETIC MATERIALS CONTAINING
FR3081864B1 (en) 2018-05-30 2022-03-18 Arianegroup Sas OBTAINING CRYSTALS OF AMMMONIUM DINITROAMIDIDE (DNA); DNA CRYSTALS AND THE ENERGETIC COMPOSITES CONTAINING THEM

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5415852A (en) * 1992-01-29 1995-05-16 Sri International Process for forming a dinitramide salt or acid by reaction of a salt or free acid of an N(alkoxycarbonyl)N-nitroamide with a nitronium-containing compound followed by reaction of the intermediate product respectively with a base or alcohol
WO1997006099A1 (en) * 1995-08-08 1997-02-20 Försvarets Forskningsanstalt Method of preparing dinitramidic acid and salts thereof
US5659080A (en) * 1995-05-26 1997-08-19 Nissan Motor Co., Ltd. Synthetic method for forming ammonium dinitrammide (ADN)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5587553A (en) * 1994-11-07 1996-12-24 Thiokol Corporation High performance pressable explosive compositions
US5801453A (en) * 1996-06-11 1998-09-01 United Technologies Corporation Process for preparing spherical energetic compounds
US5759458A (en) * 1996-07-26 1998-06-02 Thiokol Corporation Process for the manufacture of high performance gun propellants

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5415852A (en) * 1992-01-29 1995-05-16 Sri International Process for forming a dinitramide salt or acid by reaction of a salt or free acid of an N(alkoxycarbonyl)N-nitroamide with a nitronium-containing compound followed by reaction of the intermediate product respectively with a base or alcohol
US5659080A (en) * 1995-05-26 1997-08-19 Nissan Motor Co., Ltd. Synthetic method for forming ammonium dinitrammide (ADN)
WO1997006099A1 (en) * 1995-08-08 1997-02-20 Försvarets Forskningsanstalt Method of preparing dinitramidic acid and salts thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013043099A3 (en) * 2011-09-22 2013-06-20 Monogel Ab Process for manufacturing particles and particles thereby manufactured

Also Published As

Publication number Publication date
WO1999021793A1 (en) 1999-05-06
SE9703928L (en) 1999-04-29
AU9771698A (en) 1999-05-17
SE9703928D0 (en) 1997-10-28
SE512396C2 (en) 2000-03-13
WO1999021794A1 (en) 1999-05-06
AU9771798A (en) 1999-05-17
AU9771598A (en) 1999-05-17

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