NO175145B - Process for Purification of 2,2 ', 4,4', 6,6'-Hexanitro Still Life (HNS) - Google Patents
Process for Purification of 2,2 ', 4,4', 6,6'-Hexanitro Still Life (HNS)Info
- Publication number
- NO175145B NO175145B NO914749A NO914749A NO175145B NO 175145 B NO175145 B NO 175145B NO 914749 A NO914749 A NO 914749A NO 914749 A NO914749 A NO 914749A NO 175145 B NO175145 B NO 175145B
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- hns
- acetonitrile
- solvent
- hexanitro
- purification
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- 238000000034 method Methods 0.000 title claims description 18
- 238000000746 purification Methods 0.000 title 1
- YSIBQULRFXITSW-OWOJBTEDSA-N 1,3,5-trinitro-2-[(e)-2-(2,4,6-trinitrophenyl)ethenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1\C=C\C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O YSIBQULRFXITSW-OWOJBTEDSA-N 0.000 claims description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000002360 explosive Substances 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000005474 detonation Methods 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZASQDXIJRKCNQS-UHFFFAOYSA-N 1,2,3,4,5-pentanitro-6-(1-nitro-2-phenylethyl)benzene Chemical group [O-][N+](=O)C=1C([N+]([O-])=O)=C([N+]([O-])=O)C([N+]([O-])=O)=C([N+]([O-])=O)C=1C([N+](=O)[O-])CC1=CC=CC=C1 ZASQDXIJRKCNQS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000000015 trinitrotoluene Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Description
Oppfinnelsen angår en fremgangsmåte for å rense urent 2,2',4,4',6,6'-hexanitrostilben (HNS). The invention relates to a method for purifying impure 2,2',4,4',6,6'-hexanitrostilbene (HNS).
Søkningen etter sprengstoffer hvis egenskaper ikke forandres selv når de utsettes for høye temperaturer i lengre tid, og som derfor skulle kunne egne seg for anvendelse innenfor romteknologien og innenfor olje- og gassutvinning, har rettet interessen mot 2,2',4,4',6,6'-hexanitrostilben (HNS) The search for explosives whose properties do not change even when exposed to high temperatures for a long time, and which would therefore be suitable for use within space technology and within oil and gas extraction, has directed interest towards 2,2',4,4', 6,6'-hexanitrostilbene (HNS)
som et lovende alternativ. I ren form har dette sprengstoff et smeltepunkt på 319°C, og det oppviser praktisk talt uforandret sprengevne selv etter at det er blitt oppvarmet ved 232°C i 200 timer. Dessuten er det lett å fremstille ut fra 2,4,6-tri-nitrotoluen (TNT), f.eks. i henhold til den fremgangsmåte som beskrives i US patentskrift nr. 3 505 413. I henhold til denne fremgangsmåte fås det imidlertid et ikke helt rent råprodukt, as a promising alternative. In its pure form, this explosive has a melting point of 319°C, and it exhibits practically unchanged explosive power even after being heated at 232°C for 200 hours. Moreover, it is easy to produce from 2,4,6-tri-nitrotoluene (TNT), e.g. according to the method described in US patent no. 3 505 413. According to this method, however, a crude product that is not completely pure is obtained,
HNS I, som inneholder mindre mengder TNT, hexanitrobibenzyl og andre forurensninger, og følgelig har produktet ikke helt optimale egenskaper. Dets smeltepunkt er således som regel på omkring 315°C, og dets termiske stabilitet er vesentlig dår-ligere enn for det rensede sprengstoff, HNS II. HNS I, which contains small amounts of TNT, hexanitrobibenzyl and other impurities, and consequently the product does not have completely optimal properties. Its melting point is thus usually around 315°C, and its thermal stability is significantly worse than that of the purified explosive, HNS II.
I de siste 20 år er det derfor blitt gjort betydelige anstrengelser for å finne metoder til å rense urent 2,2',4,4',6,6'-hexanitrostilben, kalt NHS I, til et renere produkt definert i US Military Standard W5 5003 F, kalt HNS In the last 20 years, considerable efforts have therefore been made to find methods to purify impure 2,2',4,4',6,6'-hexanitrostilbene, called NHS I, into a cleaner product defined in the US Military Standard W5 5003 F, called HNS
II. (Normverdiene for HNS II fremgår av etterfølgende tabell II. (The standard values for HNS II appear in the following table
1.) Alle disse metoder involverer enten omkrystallisering av HNS I under anvendelse av enten et organisk oppløsningsmiddel-system eller konsentrert salpetersyre, iblant med påfølgende fysikalsk behandling av det erholdte krystallinske produkt, 1.) All these methods involve either recrystallization of HNS I using either an organic solvent system or concentrated nitric acid, sometimes with subsequent physical treatment of the obtained crystalline product,
eller en ekstråksjon i kokende oppløsningsmiddel med konti-nuerlig ny utfelling av renset HNS. or an extraction in boiling solvent with continuous reprecipitation of purified HNS.
Da HNS er temmelig lite oppløselig i de fleste orga-niske oppløsningsmidler, er valget av oppløsningsmiddel for omkrystalliseringen temmelig begrenset. Det meste av det arbeide som er blitt utført, har vært rettet mot bruk av dimethylformamid (DMF), 90% HN03 og, i en viss grad, acetonitril. Dersom man anvender DMF, alene eller i kombinasjon med acetonitril, fås HNS i form av lange nåler med en temmelig lav volumvekt (0,25-0,45 gem"<3>). Omkrystallisering fra 90% HN03 finner vanligvis anvendelse ved fremstilling av HNS II, fordi dette er en relativt enkel og billig prosess. Det erkjennes imidlertid at det derved erholdte produkt praktisk talt alltid er forurenset med salpetersyre. E.E. Kilmer (NSWC/WOL TR 78-209; se også 75-142) har i en undersøkelse vist at salpetersyren kan fjernes effektivt fra krystallene gjennom hensiktsmessig vasking og tørring ved 120°C i vakuum. Han konstaterer imidlertid at det er meget lettere å oppfylle kravene ved vakuumtesten når det benyttes oppløsningsmidler som f.eks. acetonitril/toluen eller acetonitril/xylen. Kilmer har dessuten undersøkt detonasjonsegenskapene for detonerende lunte fylt med HNS II som var blitt krystallisert fra enten As HNS is rather poorly soluble in most organic solvents, the choice of solvent for the recrystallization is rather limited. Most of the work that has been done has focused on the use of dimethylformamide (DMF), 90% HN0 3 and, to some extent, acetonitrile. If DMF is used, alone or in combination with acetonitrile, HNS is obtained in the form of long needles with a rather low volume weight (0.25-0.45 gem"<3>). Recrystallization from 90% HN03 is usually used in the production of HNS II, because this is a relatively simple and inexpensive process. However, it is recognized that the product obtained thereby is practically always contaminated with nitric acid. E.E. Kilmer (NSWC/WOL TR 78-209; see also 75-142) has in a survey demonstrated that the nitric acid can be effectively removed from the crystals through appropriate washing and drying in a vacuum at 120° C. He notes, however, that it is much easier to meet the requirements of the vacuum test when solvents such as acetonitrile/toluene or acetonitrile/xylene are used. Kilmer has also investigated the detonation properties of detonating fuses filled with HNS II that had been crystallized from either
90% HNO3 eller acetonitril/toluen, alternativt acetonitril/xylen, etter varmebehandling ved 218°C, alternativt blitt utsatt for gjentatte temperaturforandringer mellom -54°C og 177°C. Han observerte at selv HNS II med en så liten restmengde som 0,01% HNO3, ga en nedsatt detonasjonshastighet etter gjentatte temperaturforandringer, eller sågar etter normal lagring i fire år. En oppvarming til 218°C førte videre til nedsatt detonasjonshastighet samt detonasjonssvikt etter 20 h p.g.a. kjemisk nedbrytning (<20% HNS var i behold etter 20 h). I motsetning hertil var HNS II som var erholdt ved omkrystallisering med acetonitril/toluen eller acetonitril/xylen,, resi-stent overfor varmebehandling, dvs. at ingen forandring i de-tonasjonshastigheten ble iakttatt verken etter 264 timer ved 218°C eller etter 100 temperatursykluser ifølge ovenstående. 90% HNO3 or acetonitrile/toluene, alternatively acetonitrile/xylene, after heat treatment at 218°C, alternatively exposed to repeated temperature changes between -54°C and 177°C. He observed that even HNS II with as little residual amount as 0.01% HNO3 gave a reduced detonation rate after repeated temperature changes, or even after normal storage for four years. Heating to 218°C further led to reduced detonation speed and detonation failure after 20 h due to chemical degradation (<20% HNS was retained after 20 h). In contrast, HNS II obtained by recrystallization with acetonitrile/toluene or acetonitrile/xylene was resistant to heat treatment, i.e. no change in the detonation rate was observed either after 264 hours at 218°C or after 100 temperature cycles according to the above.
Den beste hittil beskrevne fremgangsmåte for fremstilling av HNS II med hensyn til det erholdte produkt er den fremgangsmåte som beskrives i US patentskrifter nr. The best method described so far for the production of HNS II with regard to the product obtained is the method described in US patent documents no.
3 699 176 og 3 832 142. Denne fremgangsmåte består i en kon-tinuerlig ekstraksjonsprosess i hvilken HNS ekstraheres fra fast HNS I med kokende acetonitril, hvoretter det til den derved erholdte oppløsning tilsettes et ikke-oppløsningsmiddel for HNS, som f.eks. toluen eller xylen. Derved utskilles HNS II fra den kokende oppløsning av acetonitril/toluen, alternativt acetonitril/xylen, mens acetonitrilet resirkuleres til ekstraksjonsprosessen. Denne fremgangsmåte gir et utmerket HNS II med en volumvekt på omkring 0,5 gem"<3>, med et smeltepunkt på 319°C og med god vakuumstabilitet (260°C), men fremgangsmåten er relativt langsom på grunn av den lave oppløselighet av HNS 3 699 176 and 3 832 142. This method consists of a continuous extraction process in which HNS is extracted from solid HNS I with boiling acetonitrile, after which a non-solvent for HNS is added to the resulting solution, such as e.g. toluene or xylene. Thereby, HNS II is separated from the boiling solution of acetonitrile/toluene, alternatively acetonitrile/xylene, while the acetonitrile is recycled to the extraction process. This process gives an excellent HNS II with a bulk weight of about 0.5 gem"<3>, with a melting point of 319°C and with good vacuum stability (260°C), but the process is relatively slow due to the low solubility of HNS
i acetonitril. in acetonitrile.
Ifølge den foreliggende oppfinnelse renses HNS I gjennom en omkrystallisering med N-methylpyrrolidon (1-methyl-2-pyrrolidon) som oppløsningsmiddel. According to the present invention, HNS I is purified through recrystallization with N-methylpyrrolidone (1-methyl-2-pyrrolidone) as solvent.
Med foreliggende oppfinnelse tilveiebringes det således en fremgangsmåte for å rense urent 2,2',4,4',6,6'-hexanitrostilben (HNS), kjennetegnet ved at HNS oppløses i N-methyl-pyrrolidon (l-methyl-2-pyrrolidon) og at det fra oppløsningen utfelles et krystallinsk produkt med større renhet. The present invention thus provides a method for purifying impure 2,2',4,4',6,6'-hexanitrostilbene (HNS), characterized by the fact that HNS dissolves in N-methyl-pyrrolidone (l-methyl-2- pyrrolidone) and that a crystalline product of higher purity is precipitated from the solution.
På fig. 1 gjengis et mikroskopbilde som i 200 ggr forstørrelse viser omkrystallisert HNS. In fig. 1 shows a microscope image which, at 200x magnification, shows recrystallized HNS.
N-methylpyrrolidon er tidligere blitt benyttet som et oppløsningsmiddel for oxydasjon av hexanitrostilben til HNS N-methylpyrrolidone has previously been used as a solvent for the oxidation of hexanitrostilbene to HNS
(E.E. Gilbert i Propellants and Explosives, vol. 5, 1980, side 168; US patentskrifter nr. 4 245 129, 4 243 614, 4 270 012 og 4 268 696) og for overføring av TNT til hexanitrobibenzyl, som erstatning for tetrahydrofuran i den tradisjonelle Skipp-Kap-lan-prosess (Propellants and Explosives, vol. 5, 1980, side 15), men dets anvendelse som omkrystallisasjonsmedium for HNS er ikke tidligere blitt beskrevet. Selv om N-methylpyrrolidon har en struktur som er temmelig lik strukturen av DMF, så er dets evne til å oppløse HNS nesten dobbelt så stor (oppløseligheten av HNS i 100 ml N-methylpyrrolidon: 4,3 g ved 10°C; 11,1 g ved 100°C; 17,8 g ved 125°C, mens oppløseligheten av HNS i 100 ml DMF er 6,1 g ved 100°C). Dessuten gir N-methyl-pyrrolidon et produkt med god vakuumstabilitet ved 260°C (se tabell 1). Den største ulempen med DMF er dog manglende vakuumstabilitet for det erholdte produkt. Oppløselighetsdataene viser at N-methyl-pyrrolidon burde kunne gi utbytter på henholdsvis 61% og 76% (E.E. Gilbert in Propellants and Explosives, vol. 5, 1980, page 168; US Patents Nos. 4,245,129, 4,243,614, 4,270,012 and 4,268,696) and for the transfer of TNT to hexanitrobibenzyl, as a substitute for tetrahydrofuran in the traditional Skipp-Kaplan process (Propellants and Explosives, vol. 5, 1980, page 15), but its use as a recrystallization medium for HNS has not previously been described. Although N-methylpyrrolidone has a structure quite similar to that of DMF, its ability to dissolve HNS is almost twice as great (solubility of HNS in 100 ml of N-methylpyrrolidone: 4.3 g at 10°C; 11, 1 g at 100°C; 17.8 g at 125°C, while the solubility of HNS in 100 ml DMF is 6.1 g at 100°C). In addition, N-methyl-pyrrolidone gives a product with good vacuum stability at 260°C (see table 1). The biggest disadvantage of DMF, however, is the lack of vacuum stability for the product obtained. The solubility data show that N-methyl-pyrrolidone should be able to give yields of 61% and 76% respectively
når mettede oppløsninger av HNS kjøles fra henholdsvis 100°C og 125°C til 10°C. Eksempel 1 nedenfor viser at utbytter som ligger nær det teoretiske, kan oppnås uten vanskeligheter. Utbyttene kan forbedres ytterligere gjennom tilsetning av et oppløselig-hetsreduserende middel som f.eks. klorbenzen (eksempler 2 og 3) eller toluen (eksempel 4), uten at vakuumstabiliteten havner uten-for de gjeldende normer. when saturated solutions of HNS are cooled from 100°C and 125°C to 10°C respectively. Example 1 below shows that yields close to the theoretical can be achieved without difficulty. The yields can be further improved through the addition of a solubility-reducing agent such as e.g. chlorobenzene (examples 2 and 3) or toluene (example 4), without the vacuum stability falling outside the applicable norms.
Ved omkrystallisering av HNS fra N-methyl-pyrrolidon, med eller uten anvendelse av et oppløsningsreduserende ko-opp-løsningsmiddel som toluen eller klorbenzen, erholdes som nevnt krystaller i form av nåler av den type som vises i 200 ggr forstørrelse på fig. 1. Krystallenes forhold mellom lengde og bredde er avhengig av kjølesyklusens temperaturprofil og hastigheten med hvilken et eventuelt benyttet oppløselighets-reduserende ko-oppløsningsmiddel er blitt tilsatt. En normal volumvekt blir da 0,3-0,45 gem"<3> med volum-middeldiametere (VMD) på 100-250um. When recrystallization of HNS from N-methyl-pyrrolidone, with or without the use of a dissolution-reducing co-solvent such as toluene or chlorobenzene, crystals are obtained as mentioned in the form of needles of the type shown in 200 times magnification in fig. 1. The crystals' ratio between length and width is dependent on the temperature profile of the cooling cycle and the speed with which any solubility-reducing co-solvent used has been added. A normal volume weight is then 0.3-0.45 gem"<3> with volume mean diameters (VMD) of 100-250um.
Eksempel 1 Example 1
200 g HNS ble oppløst i 1125 ml N-methylpyrrolidon ved 125°C hvoretter oppløsningen ble langsomt kjølt til 10°C. Det erholdte faste stoff ble frafiltrert, vasket med metanol (2X) og med 3% metanol i vann (3X) og deretter tørret. Utbyt-tet ble 147 g (73,5%) med en volumvekt på 0,42 gem"<3> med VMD = 251um. Vakuumtesten (260°C) ga 0,44 mig"<1> etter 20 min og 0,27 mlg"^"<1> etter 2 timer. 200 g of HNS were dissolved in 1125 ml of N-methylpyrrolidone at 125°C, after which the solution was slowly cooled to 10°C. The solid obtained was filtered off, washed with methanol (2X) and with 3% methanol in water (3X) and then dried. The yield was 147 g (73.5%) with a volume weight of 0.42 gem"<3> with VMD = 251 µm. The vacuum test (260°C) gave 0.44 mig"<1> after 20 min and 0, 27 mlg"^"<1> after 2 hours.
Eksempel 2 Example 2
400 g HNS ble oppløst i 2250 ml N-methylpyrrolidon ved 125°C. Det ble så tilsatt 2250 ml klorbenzen under mekanisk omrøring i 50 minutter, mens temperaturen ble holdt ved 125°C. Blandingen ble kjølt i luft til 65°C og deretter i isvann til 10°C. Det faste stoff ble frafiltrert, vasket med MeOH (2X) og 3% MeOH i vann (3X) og deretter tørret. Utbytte: 342 g (85,5%). Volumvekt 0,48 gem"<3>; VMD = 184um. Vakuum-test (260°C): 0,38 mig"<1> etter 20 min og 0,29 mig"1!!"1 etter 2 timer. 400 g of HNS were dissolved in 2250 ml of N-methylpyrrolidone at 125°C. 2250 ml of chlorobenzene were then added under mechanical stirring for 50 minutes, while the temperature was maintained at 125°C. The mixture was cooled in air to 65°C and then in ice water to 10°C. The solid was filtered off, washed with MeOH (2X) and 3% MeOH in water (3X) and then dried. Yield: 342 g (85.5%). Volumetric gravity 0.48 gem"<3>; VMD = 184um. Vacuum test (260°C): 0.38 mig"<1> after 20 min and 0.29 mig"1!!"1 after 2 hours.
Eksempel 3 Example 3
400 g HNS ble omkrystallisert fra N-methylpyrrolidon og klorbenzen som beskrevet i eksempel 2, bortsett fra at kjølingen fra 125°C ble foretatt helt og holdent med isvann. Utbytte: 340 g (85%). Volumvekt (0,44 gem"<3>, VMD = 193um. Vakuumtest (260°C): 0,51 mig _<1> etter 20 min og 0,12 mlg"1^1 etter 2 timer. 400 g of HNS were recrystallized from N-methylpyrrolidone and chlorobenzene as described in example 2, except that the cooling from 125°C was carried out entirely with ice water. Yield: 340 g (85%). Volumetric weight (0.44 gem"<3>, VMD = 193um. Vacuum test (260°C): 0.51 mig _<1> after 20 min and 0.12 mlg"1^1 after 2 hours.
Eksempel 4 Example 4
400 g HNS ble omkrystallisert som beskrevet i eksempel 3, bortsett fra at toluen ble benyttet istedenfor klorbenzen. Utbytte: 328 g (82%). Volumvekt 0,30 gem"<3>; VMD = 135pm. Vakuumtest (260°C): 0,51 mig"<1> etter 20 min og 0,10 mig"<1>]!"<1 >etter 2 timer. 400 g of HNS were recrystallized as described in example 3, except that toluene was used instead of chlorobenzene. Yield: 328 g (82%). Volumetric weight 0.30 gem"<3>; VMD = 135pm. Vacuum test (260°C): 0.51 mig"<1> after 20 min and 0.10 mig"<1>]!"<1 >after 2 hours .
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO914749A NO175145C (en) | 1987-01-21 | 1991-12-03 | Process for Purification of 2,2 ', 4,4', 6,6'-Hexanitro Still Life (HNS) |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8700212A SE468434B (en) | 1987-01-21 | 1987-01-21 | PROCEDURE FOR PURIFICATION OF HNS (2,2 ', 4,4', 6,6'-HEXANITROSTILBEN) AND PREPARATION OF HNSII |
NO880233A NO169770C (en) | 1987-01-21 | 1988-01-20 | PROCEDURE FOR PURIFICATION OF 2,2 ', 4,4', 6,6'-HEXANITROSTILBEN AND PREPARATION OF A VOLUME WEIGHT PRODUCT |
NO914749A NO175145C (en) | 1987-01-21 | 1991-12-03 | Process for Purification of 2,2 ', 4,4', 6,6'-Hexanitro Still Life (HNS) |
Publications (4)
Publication Number | Publication Date |
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NO914749L NO914749L (en) | 1988-07-22 |
NO914749D0 NO914749D0 (en) | 1991-12-03 |
NO175145B true NO175145B (en) | 1994-05-30 |
NO175145C NO175145C (en) | 1994-09-07 |
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Application Number | Title | Priority Date | Filing Date |
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NO914749A NO175145C (en) | 1987-01-21 | 1991-12-03 | Process for Purification of 2,2 ', 4,4', 6,6'-Hexanitro Still Life (HNS) |
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1991
- 1991-12-03 NO NO914749A patent/NO175145C/en not_active IP Right Cessation
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Publication number | Publication date |
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NO914749D0 (en) | 1991-12-03 |
NO914749L (en) | 1988-07-22 |
NO175145C (en) | 1994-09-07 |
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