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HNIW, CL 20, 六硝基六氮杂异伍兹烷

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Partially condensed, stereo, skeletal formula of hexanitrohexaazaisowurtzitane ChemSpider 2D Image | HNIW | C6H6N12O12

HNIW, CL-20

  • Molecular FormulaC6H6N12O12
  • Average mass438.185 Da
  • 1,3,4,7,8,10-hexanitrooctahydro-1H-5,2,6-(epiminomethanetriylimino)imidazo[4,5-b]pyrazine
    CAS 135285-90-4
  • Hexanitrohexaazaisowurtzitane
  • 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane
  • Octahydro-1,3,4,7,8,10-hexanitro-5,2,6-(iminomethenimino)-1H-imidazo[4,5-b]pyrazine
  • HNIW
  • 六硝基六氮杂异伍兹烷

ABOUT AUTHOR

Tomasz Gołofit

Thermochemistry, Physical Chemistry, Materials Chemistry

Warsaw University of Technology

Staff Paweł Maksimowski Wincenty Skupiński Wojciech Pawłowski Waldemar Tomaszewski Tomasz Gołofit Katarzyna Cieślak

Faculty of Chemistry, Division of High Energetic Materials, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland

Hexanitrohexaazaisowurtzitane /ˈhɛksɑːˈntrˈhɛksɑːˌæzɑːˌsˈvʊərtsɪtn/, also called HNIW and CL-20, is a nitroamine explosive with the formula C6H6N12O12. The structure of CL-20 was first proposed in 1979 by Dalian Institute of Chemical Physics.[1]In 1980s, CL-20 was developed by the China Lake facility, primarily to be used in propellants. It has a better oxidizer-to-fuel ratio than conventional HMX or RDX. It releases 20% more energy than traditional HMX-based propellants, and is widely superior to conventional high-energy propellants and explosives.

Industrial production of CL-20 was achieved in China in 2011, and it was soon fielded in propellant of solid rockets.[2] While most development of CL-20 has been fielded by the Thiokol Corporation, the US Navy (through ONR) has also been interested in CL-20 for use in rocket propellants, such as for missiles, as it has lower observability characteristics such as less visible smoke.[3]

CL-20 has not yet been fielded in any production weapons system, but is undergoing testing for stability, production capabilities, and other weapons characteristics.

Synthesis

THEN CONVERTED TO CL20, HNIW

Synthesis of CL20, HNIW

Image result for SYNTHESIS OF HNIW

505 Synthesis of CL-20: By oxidative debenzylation with cerium(IV) ammonium nitrate (CAN)

 

IPC: Int.Cl.8 C07D

 

A simple debenzylation approach has been discussed for the synthesis of hexanitrohexaazaisowurtzitane (HNIW or CL-20) one of the most powerful high explosives of today with cerium ammonium (IV) nitrate.
G M Gore, R Sivabalan*, U R Nair, A Saikia,

S Venugopalan & B R Gandhe

Image result for SYNTHESIS OF HNIW

First, benzylamine (1) is condensed with glyoxal (2) under acidic and dehydrating conditions to yield the first intermediate compound.(3). Four benzyl groups selectively undergo hydrogenolysis using palladium on carbon and hydrogen. The amino groups are then acetylated during the same step using acetic anhydride as the solvent. (4). Finally, compound 4 is reacted with nitronium tetrafluoroborate and nitrosonium tetrafluoroborate, resulting in HNIW.[4]

ChemSpider 2D Image | (3R,9R)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0~3,11~.0~5,9~]dodecane | C6H6N12O12

(3R,9R)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane

  • Molecular FormulaC6H6N12O12
  • Average mass438.185 Da
  • (3R,9R)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecan
    (3R,9R)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane
    (3R,9R)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatétracyclo[5.5.0.03,11.05,9]dodécane
    5,2,6-(Iminomethanetriylimino)-1H-imidazo[4,5-b]pyrazine, octahydro-1,3,4,7,8,10-hexanitro-, (5R,7aR)-

ChemSpider 2D Image | (3R,5S,9R,11S)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.0~3,11~.0~5,9~]dodecane | C6H6N12O12

(3R,5S,9R,11S)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane

  • Molecular FormulaC6H6N12O12
  • Average mass438.185 Da
  • (3R,5S,9R,11S)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecan
    (3R,5S,9R,11S)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane
    (3R,5S,9R,11S)-2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatétracyclo[5.5.0.03,11.05,9]dodécane
    5,2,6-(Iminomethanetriylimino)-1H-imidazo[4,5-b]pyrazine, octahydro-1,3,4,7,8,10-hexanitro-, (3aR,5S,6R,7aS)

Cocrystal product with HMX

In August 2012, Onas Bolton et al. published results showing that a cocrystal of 2 parts CL-20 and 1 part HMX had similar safety properties to HMX, but with a greater firing power closer to CL-20. [5][6]

Cocrystal product with TNT

In August 2011, Adam Matzger and Onas Bolton published results showing that a cocrystal of CL-20 and TNT had

The synthesis of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,9.03,11]-dodecane (HBIW) is the first stage in the production of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,9.03,11] dodecane (CL-20), which is the most potent explosive known today. Because of the high performance characteristics of CL-20, a number of research projects are being conducted worldwide on CL-20 synthesis, properties and applications

Scale-Up Synthesis of Hexabenzylhexaazaisowurtzitane, an Intermediate in CL-20 Synthesis

Faculty of Chemistry, Division of High Energetic Materials, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Chemical Works “NITRO−CHEM” S.A., Wojska Polskiego 65 A, 85−825 Bydgoszcz, Poland
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.7b00101
Abstract Image

After successful synthesis of hexabenzylhexaazaisowurtzitane (HBIW) on a laboratory scale (0.25 L reactor), it was performed on a multilaboratory scale (10 L reactor) and subsequently in an experimental installation in which a 300 L reactor was built. Seven syntheses were carried out in the unit on a pilot scale to produce 250 kg of HBIW. The pilot-scale syntheses ran with a yield comparable to those observed for the processes conducted on a large-laboratory scale. Some modifications were suggested that allowed for reduction of the HBIW weight unit by approximately 50%

HBIW was 89%. FTIR υ (cm–1): 3022, 2835, 1954, 1669, 1602, 1492, 1451, 1396, 1351, 1302, 1264, 1208, 1169, 1140, 1122, 1072, 1057, 1028, 1017, 986, 926, 896, 828, 792, 781, 749, 732, 698. 1H NMR (CDCl3, 400 MHz): δ 7.39–7.42 (m, 30 H, phenyl CH), 4.33 (s, 4 H, CH2), 4.26–4.27 (d, 8 H, CH2), 4.21 (s, 4 H, CH), 3.75 (s, 2, H, CH).

References

  1. Jump up^ 王征, 和霄雯 (2016-04-19). “北理工的爆轰速度 中国力量的可靠基石”. 北京理工大学新闻网.
  2. Jump up^ 黎轩平 (2016-04-23). ““我们要在宇宙空间占一个位置!””. 北京理工大学新闻网.
  3. Jump up^ Yirka, Bob (9 September 2011). “University chemists devise means to stabilize explosive CL-20”. Physorg.com. Retrieved 8 July 2012.
  4. Jump up^ Nair, U. R.; Sivabalan, R.; Gore, G. M.; Geetha, M.; Asthana, S. N.; Singh, H. (2005). “Hexanitrohexaazaisowurtzitane (CL-20) and CL-20-based formulations (review)”. Combust. Explos. Shock Waves. 41 (2): 121–132. doi:10.1007/s10573-005-0014-2.
  5. Jump up^ High Power Explosive with Good Sensitivity: A 2:1 Cocrystal of CL-20:HMX, Crystal Growth & Design (American Chemical Society), 2012, 12 (9), pp 4311–4314, DOI: 10.1021/cg3010882, Publication Date (Web): August 7, 2012, accessed 7 September 2012
  6. Jump up^ Powerful new explosive could replace today’s state-of-the-art military explosive, SpaceWar.com, 6 September 2012, accessed 7 September 2012
  7. Jump up^ Angewandte Chemie International Edition
  8. Jump up^ Things I Won’t Work With: Hexanitrohexaazaisowurtzitane

Further reading

////////////////CL 20, 135285-90-4, HNIW

Hexanitrohexaazaisowurtzitane
Partially condensed, stereo, skeletal formula of hexanitrohexaazaisowurtzitane
Ball and stick model of hexanitrohexaazaisowurtzitane
Names
IUPAC name

2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.03,11.05,9]dodecane
Other names

  • CL-20
  • Hexanitrohexaazaisowurtzitane
  • 2,4,6,8,10,12-Hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane
  • Octahydro-1,3,4,7,8,10-hexanitro-5,2,6-(iminomethenimino)-1H-imidazo[4,5-b]pyrazine
  • HNIW
  • Octahydro-1,3,4,7,8,10-hexanitro-5,2,6-(iminomethenimino)-1H-imidazo[4,5-b]pyrazine
    5,2,6-(Iminomethenimino)-1H-imidazo[4,5-b]pyrazine, octahydro-1,3,4,7,8,10-hexanitro-
    isowurtzitane, hexanitrohexaaza-
    Octahydro-1,3,4,7,8,10-hexanitro-5,2,6-(iminomethenimino)-1H-imidazo(4,5-b)pyrazine
Identifiers
3D model (JSmol)
Abbreviations CL-20, HNIW
ChEBI
ChemSpider
ECHA InfoCard 100.114.169
Properties
C
6N
12H
6O
12
Molar mass 438.1850 g mol−1
Density 2.044 g cm−3
Explosive data
Detonation velocity 9.38 km s−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
  • 1.Bayat, Y.; Malmir, S.; Hajighasemali, F.; Dehghani, H. Cent. Eur. J. Energy Mater. 2015, 12, 439458
  • 2.Bayat, Y.; Zarandi, M.; Khadiv-Parsi, P.; Salimi, A. Cent. Eur. J. Energy Mater. 2015, 12, 459472
  • 3.Gołofit, T.; Zyśk, K. J. J. Therm. Anal. Calorim. 2015, 119, 19311939, DOI: 10.1007/s10973-015-4418-2
  • 4.Maksimowski, P.; Adamiak, J. Propellants, Explos., Pyrotech. 2010, 35, 353358, DOI: 10.1002/prep.200900057
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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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