CS214947B1 - Method of making the 1,4-dinitro-tetrahydroimidazo/+l/4,5-d+p-imidazol-2,5+l1h,3h+p-dion by nitration of tetrahydroimidazo+l4,5-d+p-imidazol-2,5+l1h,3h+p-dion - Google Patents
Method of making the 1,4-dinitro-tetrahydroimidazo/+l/4,5-d+p-imidazol-2,5+l1h,3h+p-dion by nitration of tetrahydroimidazo+l4,5-d+p-imidazol-2,5+l1h,3h+p-dion Download PDFInfo
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- CS214947B1 CS214947B1 CS811880A CS811880A CS214947B1 CS 214947 B1 CS214947 B1 CS 214947B1 CS 811880 A CS811880 A CS 811880A CS 811880 A CS811880 A CS 811880A CS 214947 B1 CS214947 B1 CS 214947B1
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- nitric acid
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- 238000006396 nitration reaction Methods 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 27
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims abstract description 25
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 17
- YZTLXSKKFIMAKY-UHFFFAOYSA-N 3,6-dinitro-1,3a,4,6a-tetrahydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound N1C(=O)N([N+]([O-])=O)C2NC(=O)N([N+](=O)[O-])C21 YZTLXSKKFIMAKY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000011068 loading method Methods 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 230000001965 increasing effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- AVUDGGYCULGPNJ-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydroimidazo[4,5-d]imidazole Chemical group N1CNC2NCNC21 AVUDGGYCULGPNJ-UHFFFAOYSA-N 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 glycoluril nitroderivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Vynález sa týká výroby 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H)-diónu nitráciou tetrahydroimidazo [4,5 -d] -imidazol-2,5 (1H, 3H)-diónu v prostředí kyseliny dusičné), pričom podmienky nitrácie sú volené v přítomnosti dusičnanu amónneho, čo má za následok zvýšenie výťažnosti a bezpečnost procesu. Vynález je možné bez problémov využívat' pri výrobě titulnej substancie.The invention relates to the preparation of 1,4-dinitro-tetrahydroimidazo [4,5-d] imidazole-2.5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5 -d] -imidazole-2,5 (1H, 3H) -dione in the medium nitric acid), with nitration conditions are chosen in the presence of ammonium nitrate, resulting in increased yield and process safety. The invention is possible without problems in the production of the title substance.
Description
(54) Sposob výroby 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H)-diónu nitráciou tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H)-di6nu.(54) A process for producing 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H, 3H) -dione. 3H) -di6nu.
Vynález sa týká výroby 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H)-diónu nitráciou tetrahydroimidazo [4,5 -d] -imidazol-2,5 (1H, 3H)-diónu v prostředí kyseliny dusičné), pričom podmienky nitrácie sú volené v přítomnosti dusičnanu amónneho, čo má za následok zvýšenie výťažnosti a bezpečnost procesu. Vynález je možné bez problémov využívat' pri výrobě titulnej substancie.The present invention relates to the preparation of 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H) The nitration conditions are selected in the presence of ammonium nitrate, resulting in increased yield and process safety. The invention can be used without problems in the production of the title substance.
Vynález sa týká výroby 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H)-diónu nitráciou tetrahydroimidazo [4,5 -d] -imidazol-2,5 (1H, 3H)-diónu v prostředí kyseliny dusičnej, pričom podmienky sú volené tak, že priaznivo ovplyvňujú výťažok a bezpečnost procesu.The present invention relates to the preparation of 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H) -dione in a nitric acid environment, the conditions being chosen such that they favorably affect the yield and process safety.
Z literatúry je známe, že dinitroderiváty tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H)-diónu, tzv. dinitroglykolurily, označované kódom DINGU, je možné získat nitráciou v prostředí kyseliny dusičnej aj alebo kyselinou dusičnou v prostředí acetanhydridu. Z prvého uvedeného variantu rezultuje vždy zmes 1,4-, 1,6- a 1,3-dinitroderivátov (Encyclopedia of Explosives and Related Items. Vol. 6, PATR 2700, Picatinny Arsenal, Dover, 1974, str. 6117 až 6118).It is known from the literature that dinitroderivatives of tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H) -dione, the so-called. The dinitroglycolurils, referred to as the DING code, can be obtained by nitration in nitric acid or nitric acid in acetic anhydride. The first variant always results in a mixture of 1,4-, 1,6- and 1,3-dinitroderivatives (Encyclopedia of Explosives and Related Items. Vol. 6, PATR 2700, Picatinny Arsenal, Dover, 1974, pp. 6117-6118). .
Patent NSR č. 2 462 330 tiež uvažuje s možnosťou vystupovania nitroderivátov glykolurilu vo formách různých izomérov a konformérov. V uvedenom patente je spomenutá klasická dinitrácia glykolurilu kyselinou dusičnou na dinitroglykoluril s odvoláním na postup DOS 24 35 651.U.S. Pat. No. 2,462,330 also contemplates the possibility of the glycoluril nitroderivatives to exhibit in the form of various isomers and conformers. Said patent mentions the classical dinitration of glycoluril by nitric acid to dinitroglycoluril with reference to DOS 24 35 651.
Vzhladom na to, že 1,3-dinitroglykoluril je nestabilný a rozkládá sa napr. varom vo vodě, je možné sa ho pri izolácii stabilných foriem 1'ahko zbavit.Since 1,3-dinitroglycoluril is unstable and decomposes e.g. by boiling in water, it is easy to get rid of it when isolating stable forms.
Výťažok dinitroglykolurilu je vedla obecnej závislosti na reakčných podmienkach daný stabilitou glykolurilu, teda 2, 4, 6, 8-tetraazabicyklo [ 3.3.0 j oktánového skeletu v reakčnom prostředí kyseliny dusičnej, najma o koncentrácii pod 100 % hmot. pri prípadnom vysokom obsahu analytickej kyseliny dusitej, je pri nitrácii glykolurilu dominu júcou vedlajšou reakciou acidolýza a] alebo oxidačně štiepenie východzej substancie. Ako už bolo ukázané, je možné tieto nežiadúce chemické deje potlačit prídavkom močoviny do reakčnej zmesi.The yield of dinitroglycoluril is in addition to the general dependence on the reaction conditions given by the stability of glycoluril, i.e. 2,4,6,8-tetraazabicyclo [3.3.0] octane skeleton in the nitric acid reaction medium, in particular at concentrations below 100% by weight. at a possible high content of analytical nitric acid, the acidolysis α] or oxidative cleavage of the starting substance is the dominating side reaction in nitration of glycoluril. As already shown, these undesirable chemical events can be suppressed by adding urea to the reaction mixture.
Podía tohto vynálezu sposob výroby 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H)-diónu nitráciou tetrahydroimidazo [4,5-d] -imidazol-2,5 (1H, 3H]-diónu v prostředí kyseliny dusičnej sa uskutočňuje tak, že proces nitrácie prebieha v přítomnosti dusičňanu amonného, přidávaného do nitračného systému naraz alebo postupné v množstve 0,05 až 40 % hmot. s výhodou v množstve 0,8 až 18,2 °/o hmot. na hmotnost do reakcie braného tetrahydroimidazo [4,5 - d] -imidazol-2,5 (1H, 3H)-diónu.According to the present invention, a process for the preparation of 1,4-dinitro-tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5-d] -imidazole-2,5 (1H, 3H, 3H) -dione. The 3 H] -dione in the nitric acid medium is carried out in such a way that the nitration process takes place in the presence of ammonium nitrate added to the nitration system simultaneously or sequentially in an amount of 0.05 to 40% by weight, preferably in an amount of 0.8 to 18.2 °. % by weight of the reaction reacted with tetrahydroimidazo [4,5-d] imidazole-2,5 (1H, 3H) -dione.
Výhodou spůsobu podía vynálezu je skutečnost, že přítomnost dusičňanu amónneho v reakčnej zmesi priaznivo ovplyvňuje selektivitu a výťažnosť procesu v celom výhodnom rozsahu.An advantage of the process according to the invention is that the presence of ammonium nitrate in the reaction mixture favorably affects the selectivity and yield of the process over the entire preferred range.
Pri nitrácii v kyselině dusičnej 97,15 °/o-nej bolo za daných podmienok experimentu najdené, že najoptimálnejšie množstvo dusičňanu amónneho v reakčnej zmesi je 6 až 9 % hmot. navážky glykolurilu. Pri nitrácii glykolurilu v bezvodej kyselině dusičnej s obsahom 1,55 % hmot. analytickej kyseliny dusitej toto množstvo dusičňanu amónneho je zhruba 8 až 14 % hmot. navážky glykolurilu a pre kyselinu dusičnú bezvo(dú s obsahom pod 0,1 % hmot. analytickej kyseliny dusitej je optimálny prídavok uvedeného dusičňanu 4 až 6 % hmot. navážky glykolurilu. Přitom pre kyselinu dusičnú s najvyšším obsahom analytickej kyseliny dusitej je výrazné pozitivně účinný aj 40 %-ný prídavok dusičňanu amónneho, počítané na hmotnost glykolurilu, zatial čo u kyseliny dusičnej s obsahom analytickej kyseliny dusitej pod 0,2 % hmot. toto množstvo už působí výrazné negativné na výťažnosť procesu.By nitration in nitric acid 97.15% under the given experimental conditions, it was found that the most optimal amount of ammonium nitrate in the reaction mixture was 6-9% by weight. glycoluril loading. In the nitration of glycoluril in anhydrous nitric acid with a content of 1.55% by weight. This amount of ammonium nitrate is about 8 to 14 wt. Glycoluril weighing and nitric acid (below 0.1% by weight of analytical nitrous acid is optimally added 4 to 6% by weight of glycoluril weighing. For nitric acid with the highest content of analytical nitrous acid, it is also positively effective also The 40% addition of ammonium nitrate, calculated on the weight of glycoluril, while for nitric acid with an analytical nitric acid content below 0.2% by weight, this amount already has a significant negative effect on the process yield.
Vedla uvedeného ekonomického účinku je výhodou tohto vynálezu aj zvýšenie stability reakčnej zmesi a teda bezpečnosti procesu. Stabilizujúci vplyv dusičňanu amónneho pri nitračných štiepeniach v prostředí kyseliny dusičnej (čs. patentový spis č. 97100) je dobré známy a takisto dobře interpretovaný (V. Kadeřábek a J. Denkstein: Coll. Czech. Chem. Commun. 1960, 25, 1070).In addition to said economic effect, the advantage of the present invention is also an increase in the stability of the reaction mixture and hence of process safety. The stabilizing effect of ammonium nitrate in nitrous cleavage in nitric acid media (U.S. Pat. No. 97100) is well known and also well interpreted (V. Kadeřábek and J. Denkstein: Coll. Czech. Chem. Commun. 1960, 25, 1070) .
O stahilizujúcom vplyve dusičňanu amónneho a teda aj o oprávněnosti záverov z oblasti mechanizmu jeho pósobenia na zvýšenie stálosti nitračných zmesí (V. Kadeřábek a ]. Denkstein: Coll. Czech. Chem. Commun. 1960, 25, 1070] jasné svedčia aj výsledky nitrácie glykolurilu v bezvodej kyselině dusičnej s vysokým obsahom analytickej kyseliny dusitej uvedené v príkladovej časti tohto vynálezu.The strengthening effect of ammonium nitrate and thus the justification of the conclusions of the mechanism of its action on enhancing the stability of nitration mixtures (V. Kadeřábek et al., Denkstein: Coll. Czech. Chem. Commun. 1960, 25, 1070) is also evident from the results of glycoluril nitration. in anhydrous nitric acid with a high analytical nitric acid content as exemplified in the present invention.
Z vyššie uvedeného vyplývá, že tak ako močovina, může dusičňan amónny pri syntéze cyklických nitramínov nitráciou v prostředí kyseliny dusičnej přednostně vstupovat do reakcie s oxidmi dusíka a súčasne vystupovat v acido-hydrolytických rovnováhách na straně produktov, čo má vplyv na zvýšenie výťažnosti a bezpečnosti procesu nitrácii. Použitie dusičňanu amónneho je možné v nitračnom systéme spolu s močovinou.It follows from the above that, like urea, ammonium nitrate may preferentially react with nitrous oxides by nitration in the synthesis of cyclic nitramines in nitric acid environments while at the same time exerting acid-hydrolytic equilibria on the product side, thereby increasing the yield and process safety nitration. The use of ammonium nitrate is possible in the nitration system together with urea.
Nový a vyšší účinok, dosahovaný v zmysle tohto vynálezu nebol v literatúre doposial popísaný a je dokumentovaný nasledujúcimi príkladmi.The novel and higher effect achieved for the purposes of the present invention has not been described in the literature so far and is illustrated by the following examples.
Příklad 1 hmot. dielov glykolurilu (90 min sušeného pri 80 až 85 °C j sa za stálého miešania po dobu 5 až 7 minút vnáša do 500 obj. dielov kyseliny dusičnej 97,15 %-nej s obsahom pod 0,2 % hmot. analytickej kyseliny dusitej. Pri vnášaní glykolurilu je teplota vonkajším chladením udržovaná na 24 až 27 °C. Potom následuje zvýšenie teploty reakčnej zmesi vonkajším ohrevom v priebehu 6 až 7 minút na 48 až 51 °C a tomto teplotnom rozmedzí sa udržuje po dobu 45 minút. Po tejto době je nitračná zmes tenkým prúdom opatrné vedená do 2000 obj. dielov variacej vody. Rezultujúca suspenzia je 10 minút mierne refluxovaná a po vychladení na 18 až 22 °C je produkt izolovaný filtráciou, na filtri premytý vodou do neutrálnej reakcie a v tenkej vrstvě sušený 4 hod. pri 80 až 85 °C.Example 1 wt. parts of glycoluril (90 minutes dried at 80-85 ° C) are introduced into 500 parts by volume of 97.15% nitric acid containing less than 0.2% by weight of analytical nitric acid with stirring for 5 to 7 minutes. When glycoluril is introduced, the temperature is maintained at 24 to 27 ° C by external cooling, followed by an increase in the temperature of the reaction mixture by external heating to 48 to 51 ° C for 6-7 minutes, and this temperature range is maintained for 45 minutes. The nitration mixture is carefully passed into 2000 parts by volume of boiling water and the resulting suspension is slightly refluxed for 10 minutes and after cooling to 18-22 ° C the product is isolated by filtration, washed neutral with water on a filter and dried in a thin layer for 4 hours. 80-85 ° C.
Tento základný postup bol ešte paťkrát opakovaný s tým, že před vlastným vnášaním glykolurilu je v predloženej 97,15 %-nej kyselině dusičnej rozpuštěné vždy určité množstvo dusičňanu amónneho (90 min sušeného pri 85 až 90 °C). Výsledky prezentuje tabulka č. 1.This basic procedure was repeated five more times, with a certain amount of ammonium nitrate (90 minutes dried at 85-90 ° C) dissolved in the present 97.15% nitric acid before the glycoluril was introduced. The results are presented in Table no. First
Tab. č. 1Tab. no. 1
Zo závislosti výťažnosti na množstve dusičňanu amónneho je zřejmé, že prídavkom tejto látky v množstve 35,8 % hmot. na navážku glykolurilu vzniká DINGU vo výtažku rovnakom, ako v reakcii bez přídavku dusičňanu amónneho. Optimálně množstvo dusičňanu amónneho je 6 až 9 % hmot. navážky glykolurilu.It is apparent from the recovery based on the amount of ammonium nitrate that 35.8% by weight is added. DINGU is produced in the same yield as the reaction without addition of ammonium nitrate. Optimally, the amount of ammonium nitrate is 6-9% by weight. glycoluril loading.
Příklad 2Example 2
Postupuje sa ako v příklade 1, len s tým rozdielom, že je aplikovaná kyselina dusičná bezvodá s obsahom 1,55 % hmot. analytickej kyseliny dusitej. Výsledky prezentuje tabul-The procedure is as in Example 1, except that the nitric acid applied is 1.55% by weight anhydrous. analytical nitric acid. The results are presented by
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS811880A CS214947B1 (en) | 1980-11-25 | 1980-11-25 | Method of making the 1,4-dinitro-tetrahydroimidazo/+l/4,5-d+p-imidazol-2,5+l1h,3h+p-dion by nitration of tetrahydroimidazo+l4,5-d+p-imidazol-2,5+l1h,3h+p-dion |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS811880A CS214947B1 (en) | 1980-11-25 | 1980-11-25 | Method of making the 1,4-dinitro-tetrahydroimidazo/+l/4,5-d+p-imidazol-2,5+l1h,3h+p-dion by nitration of tetrahydroimidazo+l4,5-d+p-imidazol-2,5+l1h,3h+p-dion |
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| CS811880A CS214947B1 (en) | 1980-11-25 | 1980-11-25 | Method of making the 1,4-dinitro-tetrahydroimidazo/+l/4,5-d+p-imidazol-2,5+l1h,3h+p-dion by nitration of tetrahydroimidazo+l4,5-d+p-imidazol-2,5+l1h,3h+p-dion |
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