Patented Nov. 3, 1925, 1,560,427 UNITED STATES PATENT OFFICE. iRiotBERT C. MORAN, OF WOODBURY, NEW JERSEY, ASSIGNOR TO E. I. DU Pont DE - NEMOURS & CoNEPANY, OF WILMINGTON, DELAWARE, A CORPORATION of DELA WARE, EXPLOSIVE AND PROCESS OF MAKING SAME, No grawing. Application filed January 26, -1925. Serial No. 4,960. keeping the temperature at 30° to 3 s o C. To all whom it may concern: After addition is complete the mixture is Be it known that I, RoBERT C. MoRAN, a 55 citizen of the United States, and a resident heldThe finalat 40° product to 50° trinitrophenyl-nitraminoC. for A hour to 1 hour. of Woodbury, in the county of Gloucester ethyl nitrate gradually separates out and is 5 and State of New Jersey, have invented cer recovered by drowning in water, separated, tain new and useful Explosives and Proc washed and neutralized by any of the well esses of Making Same, of which the fol known methods. 60 lowing is a specification. CP The compound which I obtained by the My invention relates particularly to a above described process was a yellow pow i0 process for producing a new explosive of der which, when recrystallized from ben advantageous character and the product Zene, gave a melting point of 125°-126° C. thereof. The object of my invention is to The percentage of nitrogen as determined 65 provide new and useful explosive con on a nitrometer was 7.45 as colmpared to pounds suitable for use in detonators and 7.52%; the theoretical nitrogen content of l6 so-called booster charges. My process fur trinitrophenyl-nitramino - ethyl nita': it'. nishes a simple arid economical means of When decomposed with sodium carbonate producing new explosives of the nitramine 0. type and having a side chain attached to the and neutralized with hydrochloric acid, the amino group comprising a nitric ester of an new compound yielded picric acid, indicat 20 aliphatic alcohoi. ing three nitro groups attached to the ring. have discovered that the condensation The compound flashed when heated on a product of a primary oxyamine with dini steel spatula and detonated with great vio trochlorbenzene nitrates very readily in the lence when primed with fulminate of mer 5 presence of sulphuric and nitric acid, form cury.This new explosive is particularly well Ping a compound having a plurality of nitro adapted for use in blasting caps and in so groups attached to the ring, a nitramine called booster charges, or in any of the nu radical, and a side chair, attached to the merous explosive devices for which such 80 amino group of said radical, comprising a explosives as trilit: otoluene, picric acid nitric ester of an aliphatic alcohol. For ex and tetryl have fouild usefulness, For ex 30 ample, if I condense 2,4-dinitrochlorbenzene uple, in a blasting cap shell, I have found with amino-ethyl alcohol, I obtain dinitro that a colnpressed charge consisting of 3.5 phenylamino-ethanol / which on nitration grains of trinitrophenyl-nitrainino-ethyl ni 85 yields trinitrophenyl-nitramino-ethyl ni trate in the base of the shell and a pri; heir of trate. Although the exact details of the va 5 grains of a 90-10 mixture of fulminate, and 35 rious steps of my process may be varied, I cillorate with a superimposed inner capstile have found the following to yield a very exhibits an explosive force entirely corn satisfactory explosive compound:- arable with that given by tetry loaded aud 90 100 parts by weight of 2, 4-dinitrochlor fired under the same conditions. benzene are dissolved in 510 parts of 95% While I have described my invention v0 alcohol. 30 parts of amino-ethyl alcohol are above in detail, I wish: it to be understood then added and the solution warmed to that many changes may be made therein 70° C. 20 parts of NaOH are dissolved in without departing from the spirit of my in 30 parts of water and this solution added vention. For example, I do not wish to con slowly with agitation keeping the tempera fine myself to any particular method of con 45 ture at 70°-S0° C. The reaction mixture is densation or nitration, or to the use of any then cooled and filtered. The filtrate is co particular chlor aromatic compound or ali centrated to throw out the crystals of dini phatic amino alcohol. Thus, instead of di 0. trophenylamino-ethanol. This product is nitrochlor-benzene i may use dinitrochlor ' thenISO dissolved, keeping one thepart, teaperatureto 10 parts, inbelow 95% toluene, and in place of amino-ethyl alcohol, 35 C. and added slowly with agitation to 3 may use other saturated or unsaturated parts of nitric acid of 1.47 specific gravity monohydric alcohols containing, preferably, s 1,580,427

less than five carbon atoms, such as amino group comprising a nitric ester of an 3 methyl alcohol, amino-propyl alcohol, alcohol. amino-propenyl or iso-propenyl alcohol, etc. 7. An explosive comprising the organic The nitration should preferably be aliowed product obtained by nitrating an aromatic to proceed until a nitro group as well as a amine countaining an alcoholic side chain at nitrate group has been introduced into the tached to the amino group. V." 40 nitrophenylallino-alkanol. 8. An explosive comprising a nitro-aryl claim: nitrainino-alkyl nitrate. 1. A process of producing an explosive 9. An explosive comprising a nitro-alyl O compound which comprises condensing all nitramino-alkyl nitrate, the alkyl radical of amino aliphatic alcohol with a nitrochlor said nitrate containing from 1 to 4 carbon aromatic compound and nitrating the re atoms. suiting product of condensation. 10. An explosive comprising trinitrophe 2. A process of producing an explosive nyl-nitramino-alkyl nitrate, the alkyl radi 15 compound which comprises condensing cal of Said nitrate containing from 1 to 4 amino-ethyl alcohol with a nitrochlor aro carbon atons. matic compound and nitrating the product 11. An explosive comprising a nitrophe of condensation. nyl-nitramino-ethyl nitrate. 3. A process of producing an explosive 12. An explosive comprising trinitrophe compound which comprises condensing nyl-nitrainino-ethyl nitrate. amino-ethyl alcohol with dinitrochlorben 13. A booster charge comprising a nitro 5 zene and nitrating the resulting product of aryl-nitramino-ethyl nitrate, the aryl groups condensation. having a benzene ring nucleus, 4. A process of producing an explosive 14. 2, 4, 6-trinitrophenyl-nitramino-ethyl 2 5 compound which comprises nitrating an aro nitrate. matic anine containing all alcoholic side 15. A coupound consisting essentially of chain attached to the airl? giro. trinitrophenyl-nitramino-ethyl nitrate, said 5. A process of producing an 'N losive compound having, in powdered form, a yel compound which coin prises nitrating dini low color and, when recrystallized from its i) trophenylamino-ethanol. solution in benzene, a melting point of 125° 6. An explosive comprising an aromatic 26° C. 65 nitramine compound having a plurality of In testimony whereof I affix my signature. nitro groups attacled to the ring, and an aliphatic radical attached to the aunimo ROBERT C. MORAN.