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Ammonium dinitramide

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1744: 239: 146: 550: 545: 540: 535: 24: 1002:), the hygroscopicity is greatly reduced, but so is its performance as an explosive. ADN was mixed with amine nitrates in order to lower its melting point for use as a liquid monopropellant. The onset temperature for ADN was essentially unchanged, but some cross-reaction with the amine nitrates was observed. Kim et al. have also examined mixtures of ADN with 714: 1722: 862:
fumes. This property is also of military interest because halogen-free smoke is harder to detect. It decomposes into low-molecular-mass gases, which contributes to higher performance without creating excessive temperatures if used in gun or
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Subbiah Venkatachalam; Gopalakrishnan Santhosh; Kovoor Ninan Ninan (2004). "An Overview on the Synthetic Routes and Properties of Ammonium Dinitramide (ADN) and other Dinitramide Salts".
1717:, Stern, Alfred G.; Koppes, William M. & Sitzmann, Michael E. et al., "Process for preparing ammonium dinitramide", published 1998-02-03, assigned to 727: 1832:
Chen, Fu-yao; Xuan, Chun-lei; Lu, Qiang-qiang; Xiao, Lei; Yang, Jun-qing; Hu, Yu-bing; Zhang, Guang-Pu; Wang, Ying-lei; Zhao, Feng-qi; Hao, Ga-zi; Jiang, Wei (January 2023).
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There are at least 20 different synthesis routes that produce ammonium dinitramide. In the laboratory ammonium dinitramide can be prepared by nitration of
1834:"A review on the high energy oxidizer ammonium dinitramide: Its synthesis, thermal decomposition, hygroscopicity, and application in energetic materials" 909:, while LMP-103S is only moderately toxic. LMP-103S is UN Class 1.4S, allowing for transport on commercial aircraft, and was demonstrated on the 1101: 604: 1551: 437: 1765: 1718: 1524: 948: 1787: 253: 1298:
Finally, treatment with ammonia again splits off the desired ammonium dinitramide and regenerates the urethane starting material:
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The ADN-based monopropellant FLP-106 is reported to have improved properties relative to LMP-103S, including higher performance (
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in 2010. Special handling is not required. LMP-103S could replace hydrazine as the most commonly used monopropellant.
217: 1758: 1752: 544: 1896: 1891: 910: 1881: 153: 1769: 867:. However, the dinitramide salt is more prone to detonation under high temperatures and shock compared with the 983:. Hu et al. have investigated the possibility of reducing the hygroscopicity of ADN by co-crystallization with 955:. SRI obtained US and international patents for ADN in the mid-1990s, at which time scientists from the former 616: 539: 534: 141: 937: 696: 572: 527: 36: 793: 1833: 1714: 1693:"Room-temperature catalytically reactive ammonium dinitramide–H2O2 monopropellant for microsatellites" 1531: 1486:"Flight Heritage of Ammonium Dinitramide (ADN) Based High Performance Green Propulsion (HPGP) Systems" 1886: 1418: 1252: 1085: 855: 500: 1599:
Wang, Qiong; Wang, Xiao-Hong; Pan, Qing; Chang, Hai; Yu, Hong-Jian; Pang, Wei-Qiang (3 March 2023).
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Hu, Dongdong; Wang, Yinglei; Xiao, Chuan; Hu, Yifei; Zhou, Zhiyong; Ren, Zhongqi (September 2023).
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and ammonia. LMP-103S has 6% higher specific impulse and 30% higher impulse density than hydrazine
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Kim, Ju Won; Bhosale, Vikas Khandu; Kim, Kyu-Seop; Lee, Seung Ho; Kwon, Sejin (February 2, 2022).
612: 1442: 1218: 754: 1624:"Studies on ammonium dinitramide and 3,4-diaminofurazan cocrystal for tuning the hygroscopicity" 1406: 624: 1668:
Matsunaga, Haroki; Katoh, Katsumi; Habu, Hiroto; Noda, Masaru; Miyake, Atsumi (November 2018).
1407:"The properties of ammonium dinitramide (ADN): Part 1, basic properties and spectroscopic data" 664: 1855: 1574: 1547: 1505: 1434: 1003: 952: 941: 864: 859: 620: 490: 464: 1485: 123: 1845: 1820: 1537: 1497: 1426: 1279: 1222: 1093: 1077: 1069:
The process is performed under red light, since the compound is decomposed by higher-energy
917: 851: 789: 758: 652: 383: 311: 79: 205: 1124: 1112: 1108: 1089: 1601:"Thermal Behaviors and Interaction Mechanism of Ammonium Dinitramide with Nitrocellulose" 1422: 238: 145: 1647:"Decreasing the hygroscopicity of ammonium dinitramide (ADN) through cocrystallization" 1100:
must be added before the acid dinitramide decomposes. The final product is obtained by
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synthesis method requires four synthesis steps and results in a yield of up to 60%.
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of 259 s vs. 252 s) and density (1.362 g/cm vs. 1.240 g/cm).
1116: 1081: 1032: 995: 968: 868: 578: 1669: 1623: 1430: 337: 114: 1859: 1850: 1646: 1509: 1438: 1692: 1600: 1405:Östmark, H.; Bemm, U.; Langlet, A.; Sandén, R.; Wingborg, N. (1 June 2000). 879: 668: 1824: 1578: 1501: 590: 898: 832: 786: 766: 763: 394: 1185: 1097: 1070: 984: 945: 875: 807: 347: 172: 154: 1670:"Thermal behavior of ammonium dinitramide and amine nitrate mixtures" 1460: 836: 818: 773: 704:
Except where otherwise noted, data are given for materials in their
608: 586: 1542: 1058: 840: 102: 92: 408:α = 90.00°, β = 100.40°, γ = 90.00° 999: 951:. In 1989 ammonium dinitramide was independently synthesized at 672: 660: 582: 1737: 690: 1018:
or its salts (here potassium sulfamate) at low temperatures:
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revealed that they had discovered ADN 18 years earlier.
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Bofors company produced LMP-103S as a 1-to-1 substitute for
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and then reacted with ammonia to form the ammonium salt of
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Modern rocket fuels> PDF> Hesiserman Online Library
936:. Initially all information related to this compound was 1484:
Persson, Mathias; Anflo, Kjell; Friedhoff, Pete (2019).
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Qiao, Shen; Li, Hong-zhen; Yang, Zong-wei (June 2022).
1525:"Green Propellants Based on Ammonium Dinitramide (ADN)" 722: 372:
decomposes at 127 °C (261 °F; 400 K)
1703:(3): 1631–1644 – via Elsevier Science Direct. 990:There is also interest in using ADN to make liquid 1073:. The details of the synthesis remain classified. 1680:: 2677–2685 – via Academic Search Ultimate. 928:Ammonium dinitramide was invented in 1971 at the 1523:Larsson, Anders; Wingborg, Niklas (2011-02-14). 858:and, more importantly, does not leave corrosive 262:InChI=1S/N3O4.H3N/c4-2(5)1-3(6)7;/h;1H3/q-1;/p+1 184: 1657:(2): 84–89 – via Elsevier Science Direct. 272:InChI=1/N3O4.H3N/c4-2(5)1-3(6)7;/h;1H3/q-1;/p+1 78: 1634:: 157–164 – via Elsevier Science Direct. 905:. Additionally, hydrazine is highly toxic and 1400: 1398: 1076:Other sources report ammonium synthesis from 8: 979:. One of the challenges of using ADN is its 1674:Journal of Thermal Analysis and Calorimetry 831:. ADN decomposes under heat to leave only 237: 144: 122: 15: 1849: 1788:Learn how and when to remove this message 1611:(5) – via Academic Search Ultimate. 1571:"Dinitramide Salts: ADN Plus Other Salts" 1541: 1373: 1371: 1369: 1367: 204: 1751:This article includes a list of general 1349: 1345: 1332: 1328: 1324: 1320: 1316: 1312: 1308: 1304: 1281: 1275: 1271: 1267: 1263: 1258: 1254: 1239: 1235: 1231: 1200: 1196: 1192: 1187: 1181: 1177: 1173: 1155: 1151: 1147: 1143: 1139: 1134: 1130: 1126: 1060: 1054: 1050: 1046: 1041: 1034: 1028: 1024: 893: 889: 885: 882:by dissolving 65% ammonium dinitramide, 827: 823: 812: 802: 798: 780: 776: 769: 327: 323: 319: 1628:Chinese Journal of Chemical Engineering 1363: 930:Zelinsky Institute of Organic Chemistry 293: 258: 233: 1006:as a potential liquid monopropellant. 135: 1813:Propellants, Explosives, Pyrotechnics 1565: 1563: 1490:Propellants, Explosives, Pyrotechnics 362:93 °C (199 °F; 366 K) 265:Key: BRUFJXUJQKYQHA-UHFFFAOYSA-O 7: 994:. When ADN is co-crystalized with a 1533:Advances in Spacecraft Technologies 1221:to form ethyl dinitrocarbamate and 967:ADN can be mixed with conventional 949:intercontinental ballistic missiles 275:Key: BRUFJXUJQKYQHA-IKLDFBCSAM 175: 1757:it lacks sufficient corresponding 14: 1742: 850:oxidizer with a slightly higher 712: 548: 543: 538: 533: 22: 1107:Another synthesis known as the 708:(at 25 °C , 100 kPa). 1411:Journal of Energetic Materials 1: 1807:1999 Prentice Press, New York 1651:Energetic Materials Frontiers 1217:This is nitrated again with 1088:(oleum) containing 20% free 1461:"Green propellant LMP 103S" 897:, in 35% water solution of 1913: 1719:USA, Secretary of the Navy 1697:Advances in Space Research 1102:fractional crystallization 806:. It consists of ammonium 342:124.06 g/mol 1431:10.1080/07370650008216116 702: 682: 514: 509: 484: 430: 376: 304: 284: 249: 62: 45: 35: 30: 21: 1851:10.1016/j.dt.2022.04.006 1530:. In Hall, Jason (ed.). 1383:pubchem.ncbi.nlm.nih.gov 940:because of its use as a 599:Precautionary statements 1772:more precise citations. 401: = 11.787 Å, 51:Ammonium dinitroazanide 1825:10.1002/prep.200400043 1502:10.1002/prep.201900248 1379:"Ammonium dinitramide" 846:It makes an excellent 697:Guanylurea dinitramide 40:Azanium dinitroazanide 1805:Textbook of Chemistry 17:Ammonium dinitramide 1086:fuming sulfuric acid 856:ammonium perchlorate 747:Ammonium dinitramide 501:Friction sensitivity 405: = 5.614 Å 54:Ammonium dinitramide 1877:Explosive chemicals 1423:2000JEnM...18..123O 963:Propellant mixtures 393: = 6.914 18: 1838:Defence Technology 1219:nitrogen pentoxide 985:3,4-diaminofurazan 944:, particularly in 865:rocket propellants 755:inorganic compound 735:Infobox references 683:Related compounds 16: 1897:Soviet inventions 1892:SRI International 1798: 1797: 1790: 1575:SRI International 1553:978-953-307-551-8 1115:is nitrated with 1004:hydrogen peroxide 953:SRI International 942:rocket propellant 860:hydrogen chloride 794:dinitraminic acid 743:Chemical compound 741: 740: 573:Hazard statements 491:Shock sensitivity 465:Gibbs free energy 218:CompTox Dashboard 104:Interactive image 1904: 1882:Rocket oxidizers 1863: 1853: 1828: 1793: 1786: 1782: 1779: 1773: 1768:this article by 1759:inline citations 1746: 1745: 1738: 1727: 1726: 1725: 1721: 1711: 1705: 1704: 1688: 1682: 1681: 1665: 1659: 1658: 1642: 1636: 1635: 1619: 1613: 1612: 1596: 1590: 1589: 1587: 1586: 1577:. Archived from 1567: 1558: 1557: 1545: 1529: 1520: 1514: 1513: 1496:(9): 1073–1079. 1481: 1475: 1474: 1472: 1471: 1457: 1451: 1450: 1417:(2–3): 123–138. 1402: 1393: 1392: 1390: 1389: 1375: 1353: 1343: 1342: 1339: 1294: 1292: 1291: 1288: 1250: 1249: 1246: 1223:ammonium nitrate 1213: 1211: 1210: 1207: 1167:-nitrourethane: 1159: 1078:ammonium nitrate 1065: 911:Prisma satellite 896: 852:specific impulse 830: 817:and dinitramide 816: 805: 784: 759:chemical formula 725: 719: 716: 715: 678: 674: 670: 666: 662: 658: 654: 650: 646: 642: 638: 634: 630: 626: 622: 618: 614: 610: 606: 592: 588: 584: 580: 552: 547: 542: 537: 476: 454: 431:Thermochemistry 384:Lattice constant 331: 312:Chemical formula 242: 241: 226: 224: 208: 188: 177: 156: 148: 137: 126: 106: 82: 26: 19: 1912: 1911: 1907: 1906: 1905: 1903: 1902: 1901: 1867: 1866: 1831: 1810: 1794: 1783: 1777: 1774: 1764:Please help to 1763: 1747: 1743: 1736: 1734:Further reading 1731: 1730: 1723: 1713: 1712: 1708: 1690: 1689: 1685: 1667: 1666: 1662: 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263: 257: 256: 245: 227: 220: 211: 191: 178: 166: 129: 109: 96: 85: 72: 58: 57: 41: 12: 11: 5: 1910: 1908: 1900: 1899: 1894: 1889: 1884: 1879: 1869: 1868: 1865: 1864: 1829: 1819:(3): 178–187. 1808: 1802: 1796: 1795: 1750: 1748: 1741: 1735: 1732: 1729: 1728: 1706: 1683: 1660: 1637: 1614: 1591: 1559: 1552: 1515: 1476: 1452: 1394: 1362: 1361: 1359: 1356: 1355: 1354: 1296: 1295: 1215: 1214: 1180:−O−C(=O)−NH−NO 1161: 1160: 1150:−O−C(=O)−NH−NO 1067: 1066: 1011: 1008: 981:hygroscopicity 977:oxygen balance 973:nitrocellulose 964: 961: 925: 922: 903:monopropellant 742: 739: 738: 733: 711: 710: 706:standard state 703: 700: 699: 694: 688: 685: 684: 680: 679: 602: 597: 594: 593: 576: 571: 568: 567: 562: 557: 554: 553: 531: 526: 523: 522: 512: 511: 507: 506: 503: 497: 496: 493: 487: 486: 482: 481: 480:−150.6 kJ/mol 478: 469: 463: 460: 459: 456: 450: 444: 436: 433: 432: 428: 427: 424: 414: 411: 410: 407: 389: 387: 382: 379: 378: 374: 373: 370: 364: 363: 360: 354: 353: 350: 344: 343: 340: 334: 333: 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Retrieved 1579:the original 1532: 1518: 1493: 1489: 1479: 1468:. Retrieved 1464: 1455: 1414: 1410: 1386:. Retrieved 1382: 1297: 1216: 1164: 1162: 1106: 1080:, anhydrous 1075: 1068: 1013: 989: 966: 957:Soviet Union 927: 915: 907:carcinogenic 873: 848:solid rocket 845: 785:. It is the 750: 746: 745: 564: 516: 472: 458:−148 kJ/mol 447: 419: 402: 398: 390: 63:Identifiers 46:Other names 1887:Nitroamines 1844:: 163–195. 1770:introducing 1331:−O−C(=O)−NH 1133:−O−C(=O)−NH 1117:nitric acid 1096:other than 1082:nitric acid 1010:Preparation 996:crown ether 969:propellants 869:perchlorate 559:Signal word 305:Properties 296:.((=O))(=O) 142:100.126.585 80:140456-78-6 1871:Categories 1753:references 1715:US 5714714 1585:2012-04-15 1536:. InTech. 1470:2024-04-25 1388:2024-07-18 1358:References 1344:][N(NO 938:classified 528:Pictograms 377:Structure 352:1.81 g/cm 338:Molar mass 322:][N(NO 206:8JCB80Q5K1 115:ChemSpider 91:3D model ( 70:CAS Number 37:IUPAC name 1860:2214-9147 1605:Molecules 1510:0721-3115 1439:0737-0652 1335:+ [NH 1191:→ [CH 1045:+ [NH 880:hydrazine 772:][N(N 757:with the 657:P370+P380 653:P370+P378 645:P309+P311 641:P301+P312 519:labelling 440:formation 163:604-184-9 155:EC Number 1465:ecaps.se 1447:94304770 1242:][NH 1203:][NH 1109:urethane 971:such as 899:methanol 833:nitrogen 787:ammonium 753:) is an 510:Hazards 186:10219428 1766:improve 1419:Bibcode 1280:[NH 1230:[CH 1098:ammonia 1071:photons 946:Topol-M 932:in the 924:History 884:[NH 876:Eurenco 811:[NH 808:cations 728:what is 726: ( 691:cations 468:(Δ 348:Density 332: 318:[NH 173:PubChem 124:8394920 1858:  1755:, but 1724:  1550:  1508:  1445:  1437:  1319:+ 2 NH 1084:, and 839:, and 837:oxygen 819:anions 723:verify 720:  689:Other 565:Danger 289:SMILES 31:Names 1528:(PDF) 1443:S2CID 1138:+ HNO 1049:]N(NO 888:]N(NO 854:than 841:water 797:HN(NO 762:[ 254:InChI 93:JSmol 1856:ISSN 1548:ISBN 1506:ISSN 1435:ISSN 1323:→ CH 1262:→ CH 1253:O(NO 1251:] + 1142:→ CH 1094:base 1092:. A 1040:KHSO 1031:+ 2 1000:18C6 934:USSR 874:The 822:N(NO 790:salt 677:P501 673:P405 669:P401 665:P373 661:P372 649:P330 637:P280 633:P270 629:P264 625:P260 621:P250 617:P241 613:P240 609:P230 605:P210 591:H371 587:H302 583:H228 579:H201 505:Low 495:Low 197:UNII 1846:doi 1821:doi 1678:135 1538:doi 1498:doi 1427:doi 1284:]NO 1154:+ H 1104:. 1033:HNO 1023:KSO 918:ISP 792:of 751:ADN 517:GHS 451:298 223:EPA 176:CID 1873:: 1854:. 1842:19 1840:. 1836:. 1817:29 1815:. 1701:69 1699:. 1695:. 1676:. 1672:. 1653:. 1649:. 1632:61 1630:. 1626:. 1609:28 1607:. 1603:. 1573:. 1562:^ 1546:. 1504:. 1494:44 1492:. 1488:. 1463:. 1441:. 1433:. 1425:. 1415:18 1413:. 1409:. 1397:^ 1381:. 1366:^ 1327:CH 1307:CH 1303:CH 1278:+ 1266:CH 1234:CH 1225:: 1195:CH 1186:NH 1184:+ 1176:CH 1172:CH 1146:CH 1129:CH 1125:CH 1119:: 1057:+ 1038:→ 1027:NH 987:. 871:. 843:. 835:, 675:, 671:, 667:, 663:, 659:, 655:, 651:, 647:, 643:, 639:, 635:, 631:, 627:, 623:, 619:, 615:, 611:, 607:, 589:, 585:, 581:, 521:: 443:(Δ 426:4 397:, 1862:. 1848:: 1827:. 1823:: 1791:) 1785:( 1780:) 1776:( 1762:. 1655:3 1588:. 1556:. 1540:: 1512:. 1500:: 1473:. 1449:. 1429:: 1421:: 1391:. 1352:] 1350:2 1348:) 1346:2 1341:4 1338:+ 1333:2 1329:2 1325:3 1321:3 1317:2 1315:) 1313:2 1309:2 1305:3 1290:3 1287:− 1282:4 1276:2 1274:) 1272:2 1268:2 1264:3 1259:2 1257:) 1255:2 1248:4 1245:+ 1240:2 1236:2 1232:3 1212:] 1209:4 1206:+ 1201:2 1197:2 1193:3 1188:3 1182:2 1178:2 1174:3 1165:N 1158:O 1156:2 1152:2 1148:2 1144:3 1140:3 1135:2 1131:2 1127:3 1063:O 1061:2 1059:H 1055:2 1053:) 1051:2 1047:4 1042:4 1035:3 1029:2 1025:3 998:( 894:2 892:) 890:2 886:4 828:2 826:) 824:2 815:] 813:4 803:2 801:) 799:2 783:] 781:2 779:) 777:2 774:O 770:4 767:H 764:N 749:( 718:N 475:) 473:G 470:f 453:) 448:H 445:f 422:) 420:Z 418:( 403:c 399:b 395:Å 391:a 330:] 328:2 326:) 324:2 320:4 225:) 221:( 95:)

Index


IUPAC name
CAS Number
140456-78-6
JSmol
Interactive image
ChemSpider
8394920
ECHA InfoCard
100.126.585
Edit this at Wikidata
EC Number
PubChem
10219428
UNII
8JCB80Q5K1
CompTox Dashboard
DTXSID80161401
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Density
Melting point
Boiling point
Lattice constant
Å
Formula units
Std enthalpy of
formation

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