GB963336A - Method for preparing secondary nitramines - Google Patents

Method for preparing secondary nitramines

Info

Publication number
GB963336A
GB963336A GB31821/60A GB3182160A GB963336A GB 963336 A GB963336 A GB 963336A GB 31821/60 A GB31821/60 A GB 31821/60A GB 3182160 A GB3182160 A GB 3182160A GB 963336 A GB963336 A GB 963336A
Authority
GB
United Kingdom
Prior art keywords
alkyl
nitramine
nitrazaalkyl
nitroalkyl
aralkyl
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.)
Expired
Application number
GB31821/60A
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.)
Aerojet Rocketdyne Inc
Original Assignee
Aerojet General Corp
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 Aerojet General Corp filed Critical Aerojet General Corp
Publication of GB963336A publication Critical patent/GB963336A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7868—Nitrogen containing nitro groups
    • 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
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B43/00—Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
    • C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
    • C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
    • C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
    • C06B45/105—The resin being a polymer bearing energetic groups or containing a soluble organic explosive
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic

Abstract

Secondary nitramines of the formula RN(NO2).R1 where R and R1 are alkyl, cyano alkyl, cyanonitrazaalkyl, nitrazaalkyl, nitroalkyl, alkenyl, aryl, aralkyl, cycloalkyl, heterocyclic or halo alkyl radicals, are prepared by reacting the amine RNHR1, where R and R1 are alkyl, cyanoalkyl, cyanonitrazalkyl, nitrazaalkyl, cyanoazaalkyl, azaalkyl, nitroalkyl, alkenyl, aryl, aralkyl, cycloalkyl, heterocyclic or haloalkyl radicals, with nitric acid to form the amine nitrate, and adding to the latter a dehydrating agent (such as acetic anhydride, sulphuric acid, ketene, polyphosphoric acid, SO3, trifluoroacetic anhydride and propanoic anhydride) and a halide catalyst (such as HCl, acetyl chloride, pyridinium chloride, AlCl3, NaCl, KBr, CaCl2 and Mg Br2) at 5-30 DEG C. Examples prepare (1) nitrimino dipropionitrile; (2) 4-nitrazapentanonitrile; (3) 3-nitrazabutyronitrile; (4) 4, 7-dinitraza-1, 10-decane dinitrile; (5) propyl 2-nitropentyl nitramine; (6) chloroethyl vinyl nitramine; (7) naphthyl pyrryl nitramine; and (8) cyclohexyl b -phenylethyl nitramine. Other products are listed also. Specification 615,310 is referred to.ALSO:Mononitrile compounds falling within the formula RN(NO2).R1, where R and R1 are alkyl, cyanoalkyl, cyanonitrazaalkyl, nitrazaalkyl, nitroalkyl, alkenyl, aryl, aralkyl, cycloalkyl, heterocyclic or haloalkyl radicals (see Division C2) are useful as plasticizers for polyurethanes containing nitro groups; the nitropolymers can be polymerized in the presence of the plasticizer, or the plasticizer can be mixed into the nitropolymer after its polymerization. Dinitrile compounds falling within the above formula can be hydrolysed to the bicarboxylic acids, these converted to the corresponding diisocyanates, and the latter reacted with diols such as ethylene glycol to give nitro-substituted polyurethanes. Specification 615,310 is referred to.
GB31821/60A 1959-10-01 1960-09-15 Method for preparing secondary nitramines Expired GB963336A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US84481659A 1959-10-01 1959-10-01

Publications (1)

Publication Number Publication Date
GB963336A true GB963336A (en) 1964-07-08

Family

ID=25293706

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31821/60A Expired GB963336A (en) 1959-10-01 1960-09-15 Method for preparing secondary nitramines

Country Status (3)

Country Link
CH (1) CH388335A (en)
FR (1) FR1268309A (en)
GB (1) GB963336A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6309484B2 (en) * 1997-02-08 2001-10-30 Diehl Stiftung & Co. Propellent charge powder for barrel-type weapons

Also Published As

Publication number Publication date
CH388335A (en) 1965-02-28
FR1268309A (en) 1961-07-28

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