CS238442B1 - 1,3,5,7-tetranitro-1,3,5,7-tetraazacylooctane production method - Google Patents
1,3,5,7-tetranitro-1,3,5,7-tetraazacylooctane production method Download PDFInfo
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- CS238442B1 CS238442B1 CS1001083A CS1001083A CS238442B1 CS 238442 B1 CS238442 B1 CS 238442B1 CS 1001083 A CS1001083 A CS 1001083A CS 1001083 A CS1001083 A CS 1001083A CS 238442 B1 CS238442 B1 CS 238442B1
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- tetraazacyclooctane
- tetranitro
- octogen
- dadn
- diacetyl
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- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims abstract description 22
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000006396 nitration reaction Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 9
- KFZNAQUHJDVURZ-UHFFFAOYSA-N 1-(5-acetyl-3,7-dinitro-1,3,5,7-tetrazocan-1-yl)ethanone Chemical compound CC(=O)N1CN([N+]([O-])=O)CN(C(C)=O)CN([N+]([O-])=O)C1 KFZNAQUHJDVURZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims 1
- 239000000028 HMX Substances 0.000 abstract description 15
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 14
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
- UFHGABBBZRPRJV-UHFFFAOYSA-N Hydroxysanguinarine Chemical compound C12=CC=C3OCOC3=C2C(=O)N(C)C(C2=C3)=C1C=CC2=CC1=C3OCO1 UFHGABBBZRPRJV-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- ZNXALBRTUNJVIH-UHFFFAOYSA-N 1,3,5,7-tetrazocane Chemical group C1NCNCNCN1 ZNXALBRTUNJVIH-UHFFFAOYSA-N 0.000 description 1
- BUPCSJIRCTYAHP-UHFFFAOYSA-N 1-(3-acetyl-1,3,5,7-tetrazabicyclo[3.3.1]nonan-7-yl)ethanone Chemical compound C1N2CN(C(=O)C)CN1CN(C(C)=O)C2 BUPCSJIRCTYAHP-UHFFFAOYSA-N 0.000 description 1
- UOYIYWCAYFTQLH-UHFFFAOYSA-N 3,7-dinitro-1,3,5,7-tetrazabicyclo[3.3.1]nonane Chemical compound C1N2CN([N+](=O)[O-])CN1CN([N+]([O-])=O)C2 UOYIYWCAYFTQLH-UHFFFAOYSA-N 0.000 description 1
- 241000566515 Nedra Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011988 third-generation catalyst Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Vynález pojednává o výrobo 1,3,5,7-tetranitro 1,3,5,7-tetraazacyklooktánu, zvaného oktogén, nitračným štiepením 1,5-diacetyl- -3,7-dinitrO-l,3,5,7-tetraazacyklooktánu, označovaného DADN, kyselinou dusičnou s obsahom oxidu dusičného, pri čom je do reakčného systému přidávaný dikyandiamid v množstve 0,05 až 11 % hmot., počítané na východiskové množstvo DADN. Postup je použitelný vo výrobě oktogénu, no má význam predovšetkým pre vývoj nových postupov výroby tejto substancie.The invention relates to the production of 1,3,5,7-tetranitro 1,3,5,7-tetraazacyclooctane, called octogen, by nitration of 1,5-diacetyl- -3,7-dinitrole-1,3,5,7-tetraazacyclooctane, denoted DADN, nitric acid s nitric oxide, where it is reactive dicyandiamide v from 0.05 to 11 wt starting amount of DADN. The procedure is applicable in the production of octogen, but it is important in particular for the development of new production processes of this substance.
Description
(54) Sposob výroby l,3,5,7-tetranitro-l,3,5,7-tetraazacyklooktánu(54) Production method for 1,3,5,7-tetranitro-1,3,5,7-tetraazacycloctocane
Vynález pojednává o výrobo 1,3,5,7-tetranitro 1,3,5,7-tetraazacyklooktánu, zvaného oktogén, nitračným štiepením 1,5-diacetyl-3,7-dinitrO-l,3,5,7-tetraazacyklooktánu, označovaného DADN, kyselinou dusičnou s obsahom oxidu dusičného, pri čom je do reakčného systému přidávaný dikyandiamid v množstve 0,05 až 11 % hmot., počítané na východiskové množstvo DADN. Postup je použitelný vo výrobě oktogénu, no má význam predovšetkým pre vývoj nových postupov výroby tejto substancie.The present invention relates to the production of 1,3,5,7-tetranitro 1,3,5,7-tetraazacyclooctane, called octogen, by nitration cleavage of 1,5-diacetyl-3,7-dinitrO-1,3,5,7-tetraazacyclooctane, % of DADN, a nitric oxide-containing nitric acid, and 0.05 to 11% by weight of dicyandiamide, calculated on the starting amount of DADN, is added to the reaction system. The process is applicable in the production of octogen but is of particular importance for the development of new processes for the manufacture of this substance.
Vynález sa týká spůsobu výroby 1,3,5,7-tetranitro-l,3,5,7-tetraázacyklooktánu nitrolýzou l,5-diacetyl-3,7-dinitro-l,3,5,7-tetraazacyklooktánu kyselinou dusičnou, obsahujúcou oxid dusičný, za přítomnosti dikyanidu v reakčnej zmesi.The present invention relates to a process for the preparation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane by nitrolysis of 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane with nitric acid containing nitric oxide, in the presence of dicyanide in the reaction mixture.
Běžný spůsob výroby l,3,5,7-tetranitro-l,3,5,7-tetraazacyklooktánu, nazývaného tiež oktogén a označovaného kódom HMX, spočívá v nitrolýze hexametylentetraminu a/alebo l,5-metano-3,7-dinitro-l,3,5,7-tetraazacyklooktánu (bibliografiu viď v E. Ju. Orlova: Oktogen — termostojkoe vzryvčatoe veščestvo: Izdat. Nedra, Moskva, 1987). V poslednom desaťročí sa však čoraz váčšou mierou pozornost upriamuje na procesy, ktorými sa oktogén získává cez l,5-dialkanoyl-3,7-metano-l,3,5,7-tetraazacyklooktány; ich příprava je popísaná na příklad v prácach: V. I. Siele, M. Warmann a E. E. Gilbert: J. Heterocycl. Chem. 1974, 11, 237; U. S. pat. 3 850 923 a 3 849 414.A common process for the production of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane, also called octogen, also referred to as HMX code, consists in nitrolysis of hexamethylenetetramine and / or 1,5-methano-3,7-dinitro- 1,3,5,7-tetraazacyclooctane (bibliography see E. Ju. Orlova: Oktogen - termostojkoe vzryvčatoe vsechestvo: Izdat. Nedra, Moscow, 1987). In the last decade, however, attention has been increasingly focused on the processes by which octogen is obtained through 1,5-dialkanoyl-3,7-methano-1,3,5,7-tetraazacycloctocanes; their preparation is described, for example, in V.I. Siele, M.Warmann and E.E. Gilbert: J. Heterocycl. Chem. 1974, 11, 237; U.S. Pat. 3,850,923 and 3,849,414.
Velmi atraktívnou sa javí metoda syntézy oktogénu, vychádzajúca z l,5-diacetyl-3,7-dinitro-l,3,5,7-tetraazacyklooktánu ako medziproduktu (U. S. pat. 3 939 148). Tento medzi produkt rezultuje z hexametylentetraminu cez l,5-diacetyl-3,7-metano-l,3,5,7-tetraazacyklooktán vo výťažkoch 91 až 98 % oproti teorii (U. S. pat. 3 850 923 a 3 926 953); jeho kódové označenie je DADN. Nitrolýza 1,5-diacetyl-3,7-dinitro-l,3,5,7-tetraazacyklooktánu kyselinou dusičnou, obsahujúcou až 50 percent hmot. oxidu dusičného, v závislosti od reakčných podmienok a v malej miere od zdroja oxidu dusičného, poskytuje oktogén v 41 až 98 % výtažku oproti teorii (U. S. pat. 3 939 148). Nevýhodou tohto známého postupu nitrolýzy DADN je fakt, že pre zabezpečenie vysokej výťažnosti oktogénu je nutné aplikovat čerstvo destilovánu kyselinu dusičnú bezvodú vo vefkom přebytku oproti teorii (U. S. pat. 3 939 148). Tak na příklad pre získanie 1 hmot, dielu oktogénu 100%-nej čistoty a vo výtažku 98 % oproti teorii je potřeba 34,5 hmot. dielu čerstvo destilovanej kyseliny dusičnej a 11,5 hmot. dielu oxidu fosforečného.A method of octogen synthesis starting from 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacycloctocane as an intermediate (U.S. Pat. No. 3,939,148) appears to be very attractive. This intermediate results from hexamethylenetetramine via 1,5-diacetyl-3,7-methano-1,3,5,7-tetraazacyclooctane in yields of 91-98% over theory (U.S. Pat. Nos. 3,850,923 and 3,926,953); its codename is DADN. Nitrolysis of 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane with nitric acid containing up to 50% by weight of nitric acid. nitric oxide, depending on the reaction conditions and to a small extent on the nitric oxide source, provides octogen in 41 to 98% yield compared to theory (U.S. Pat. No. 3,939,148). A disadvantage of this known nitrolysis process of DADN is that fresh distilled anhydrous nitric acid must be applied in large excess over theory to ensure high octogen recovery (U.S. Pat. No. 3,939,148). Thus, for example, 34.5 wt.% Are required to obtain 1 wt.% Of the 100% octogen and an 98% yield. % of freshly distilled nitric acid and 11.5 wt. % of phosphorus pentoxide.
Hlavnou vedfajšou reakciou nitrolýzy 1,5-diacetyl-3,7-dinitro-l,3,5,7-tetraazacyklooktánu je štiepenie 1,3,5,7-tetraazacyklooktánového skeletu. Okrem reakčných podmienok v obecnom zmysle slova je priebeh tejto nežiadúcej reakcie závislý i na druhu zdroja oxidu dusičitého (kombinácia kyseliny dusičnej a oxidu fosforečného, alebo oxidu sírového, alebo anhydridu kyseliny trifluóroctovej alebo roztok oxidu dusičitého v kyselině dusičnej — viď U. S. pat. 3 939 148).The major side reaction of the nitrolysis of 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane is the cleavage of the 1,3,5,7-tetraazacyclooctane skeleton. In addition to the reaction conditions in the general sense, the course of this undesired reaction also depends on the kind of nitrogen dioxide source (a combination of nitric acid and phosphorus pentoxide or sulfur trioxide or trifluoroacetic anhydride or a solution of nitrogen dioxide in nitric acid - see US Pat. ).
Pódia najnovších poznatkov je výťažnosť a bezpečnost procesu nitračného štiepenia a/alebo nitrácie amínov, ich N-derivátov a amidov, na cyklické nitramíny priaznivo ovplyvnené prítomnosťou niektorých aditív (vid na příklad čs. autorské osvedčenia č. 206 382, 213 509, 214 311, 218 703 a ďalšie), ktoré tu figuruji! v podstatě ako katalyzátory tretej generácie. V zmysle tohto vynálezu je výroba l,3,5,7-tetranítro-l,3,5,7-tetraazacyklooktánu uskutočňovaná nitračným štiepením l,5-diacetyl-3,7-dinitro-l,3,5,7-tetraazacyklooktánu kyselinou dusičnou, obsahujúcou oxid dusičný, za přítomnosti dikyanidu, přidávaného do reakčného systému v množstve 0,05 až 11,0 % hmot., počítané na hmotnost do reakcie braného 1,5-diacetyl-3,7-dinitro-l,3,5,7-tetraazacyklooktánu.Recent knowledge is the yield and safety of the nitrous cleavage and / or nitration process of amines, their N-derivatives and amides, to cyclic nitramines favorably affected by the presence of certain additives (see, for example, US Patent Nos. 206 382, 213 509, 214 311, 218 703 and others) that I figure here! essentially as third generation catalysts. For the purposes of the present invention, the production of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane is accomplished by nitration of 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane by acid nitric oxide containing nitric oxide in the presence of dicyanide added to the reaction system in an amount of 0.05 to 11.0% by weight, calculated on the weight of the reaction taken of 1,5-diacetyl-3,7-dinitro-1,3,5 7-tetraazacyclooctane.
Výhodou postupu podlá tohto vynálezu je tá skutočnosť, že sa nevyžaduje čerstvo destilovaná kyselina dusičná, pri čom je dosiahnuté zvýšenie výtažnosti.An advantage of the process of the present invention is that freshly distilled nitric acid is not required, and an increase in yield is achieved.
Vyšší účinok, dosahovaný v zmysle tohto vynálezu, nebol v literatuře doposial popísaný; dokumentujú ho nasledujúce příklady, ktoré.-však v žiadnom případe nevylučujú variabilitu spůsobu výroby podlá tohto vynálezu.The higher effect achieved for the purposes of the present invention has not been described so far in the literature; it is illustrated by the following examples, which in no way exclude the variability of the production method according to the invention.
Příklad 1Example 1
K 200 objem, dielom kyseliny dusičnej 98,1 percentnej s obsahom pod 0,3 % hmot. analytickej kyseliny dusitej, předloženým v nitračnom aparáte, je za, miešania a chladenia pod teplotou 40 °C vnesených 100 hmot. dielov oxidu fosforečného. Do rezultujúceho roztoku je jednorázovo vnesených 20 hmot. dielov l,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyklooktánu (DADN) a teplota reakčnej zme si je opatrné zvýšená na 54 až 57 °C, na ktorých je udržiavaná 30 minút (všetky predošlé operácie realizované za dobrého miešania). Potom je obsah nitračného aparátu nahatý do· 1500 objem, dielov 20 až 22 °C teplej vody a rezultujúca zmes je filtrovaná.K 200 volume, part by volume of nitric acid 98.1% with a content below 0.3% by weight. of analytical nitric acid, presented in the nitration apparatus, 100 wt. parts of phosphorus pentoxide. 20 wt. parts of 1,5-diacetyl-3,7-dinitro-1,3,5,7-tetraazacyclooctane (DADN) and the temperature of the reaction mixture is carefully raised to 54-57 ° C for 30 minutes (all previous operations). with good mixing). Thereafter, the nitration apparatus content is loaded into · 1500 volumes, 20 to 22 ° C parts of warm water, and the resulting mixture is filtered.
Produkt na filtr! je premývaný vodou až do neutrálnej reakcie filtrátu a potom je .3 hod. sušený pri 90 až 95 °C. Takto získaný technický oktogén je možné velmi malých množstiev vedfajších produktov zbavit jeho zohrievaním v suspenzii v 70%-nej kyselině dusičnej.Filter Product! The reaction mixture is washed with water until the filtrate is neutralized and then dried at 90-95 ° C for 3 hours. The technical octogen thus obtained can be freed of very small amounts of by-products by heating it in suspension in 70% nitric acid.
Uvedený základný postup je opakovaný vždy s aplikáciou východiskového DADN, modifikovaného určitým množstvom dikyandiamidu. Výsledky prezentuje tabelárny přehrad:This basic procedure is repeated with the application of the starting DADN, modified with a certain amount of dicyandiamide. Tabular dams present the results:
Množstvo dikyandiamidn DADN hmot. hmot. % na dlely návažok DADNQuantity of dicyandiamide DADN wt. wt. % for long DADN bait
Výťažok oktogénu hmot. % oproti diely teoriiYield of octogen mass. % versus part theory
Nekorigovaná teplota topenia oktogénu (°C)Uncorrected octogen melting point (° C)
Příklad 2Example 2
K 110 objem. dielOm kyseliny dusičnej rovnakcj kvality, ako v příklade 1 je za rovnakých podmienok, ako v příklade 1, nadávkovaných 80 hmot. dielov oxidu fosforečného, a potom do rezultujúceho roztoku 10 hmot. dielov DADN. Po 30-minútovom miešaní pri teplote 59 až 61 °C je reakčná zmes naliatá do 1000 objem, dielov vody cca 20 °C teplej, Rezultujúca suspenzia je spracované, ako v příklade 1. Rezultuje 8,4 hmot. dielov oktogénu o teplote topenia 279 až 280 °C za rozkladu; uvedený výťažok představuje 82,35 % oproti teorii.K 110 vol. 80 parts by weight of nitric acid of the same quality as in Example 1 are dosed under the same conditions as in Example 1. parts by weight of phosphorus pentoxide, and then to the resulting solution 10 wt. DADN parts. After stirring for 30 minutes at 59 to 61 ° C, the reaction mixture is poured into 1000 volumes, parts of water about 20 ° C warm. The resulting suspension is treated as in Example 1. 8.4 wt. parts of octogen, m.p. 279 DEG-280 DEG C. with decomposition; said yield represents 82.35% compared to theory.
Příklad 3Example 3
Postupuje sa ako v příklade 2, len aplikovaný východiskový DADN obsahuje 0,8 hmot, diela dikyandiamidu. Z reakce rezultuje 8,5 hmot. diela októgenu o teplote topenia 280 až 281CC za rozkladu; uvedený výťažok představuje 83,33 % oproti teorii [t. j. pri aplikácii 8 % hmot. dikyandiamidu na návažok DADN).The procedure is as in Example 2, except that the starting DADN applied contains 0.8 parts by weight of dicyandiamide. The reaction resulted in 8.5 wt. parts of octogene, m.p. 280 DEG- 281 DEG C. with decomposition; said yield represents 83.33% of theory [i.e. when applied at 8% wt. Dicyandiamide (DADN).
Claims (1)
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| CS1001083A CS238442B1 (en) | 1983-12-27 | 1983-12-27 | 1,3,5,7-tetranitro-1,3,5,7-tetraazacylooctane production method |
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| CS1001083A CS238442B1 (en) | 1983-12-27 | 1983-12-27 | 1,3,5,7-tetranitro-1,3,5,7-tetraazacylooctane production method |
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1983
- 1983-12-27 CS CS1001083A patent/CS238442B1/en unknown
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