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Methyl nitrate

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35: 251: 176: 48: 57: 772: 739:"Wildu mit wasser schyessen // daß du kein pulfer prauch // est vnd sterker und waiter // mit schewst dann als du daß aller // pest pulfer hast das yemann gehab // en mag und ye gemacht wurd so ny // salpeter und distillier den mit wasser // vnd nym oleo benedicto dazu auch … // … vnd zunt sie an mit sinnen das du davon kommen magst … // …mit disem wasser schewst du dreytousent schrit weit … // … es ist gar köstlich…" 747:"Do you want to shoot with water // so that you don't need powder // and stronger and further // you shoot than the very // best powder somebody might have had ever // and was made ever // so take salpetre and distill it with water // and also take oleo benedicto (the oil of Benedicus) // and ignite it with the intention that you may get off ... with this water you will shoot threethousand foot // it is so delicious" 783: 461: 701:
at a constant rate and so its composition would not change over time. It presents a slight explosive danger (it is somewhat difficult to detonate) and does not detonate easily via shock.
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Methyl nitrate has not received much attention as an explosive, but as a mixture containing 25% methanol it was used as rocket fuel and volumetric explosive under the name Myrol in
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in 1933. Gartz shows in a recent work that only methyl nitrate with its production and explosion potential can represent the famous and mysterious "shooting water" from the German
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Reichel, Marco; Krumm, Burkhard; Vishnevskiy, Yury V.; Blomeyer, Sebastian; Schwabedissen, Jan; Stammler, Hans-Georg; Karaghiosoff, Konstantin; Mitzel, Norbert W. (2019-12-16).
616:. However, the process is usually run at a slightly higher temperature and the mixture is stirred mechanically on an industrial scale instead of with compressed air. 642:. When ignited it burns extremely fiercely with a gray-blue flame. Methyl nitrate is a very strong explosive with a detonation velocity of 6,300 m/s, like 474: 919: 1178: 630:, while also producing nitromethane. Oxidation of nitromethane using nitrogen dioxide in an inert atmosphere can also yield methyl nitrate. 300: 622:
Methyl nitrate is also the product of the oxidation of some organic compounds in the presence of nitrogen oxides and chlorine, namely
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Despite the superior explosive properties of methyl nitrate, it has not received application as an explosive due mostly to its high
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Electrolytic production methods have been reported involving electrolyzing sodium acetate and sodium nitrate in acetic acid.
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and nitric acids. The first procedure is not preferred due to the great explosion danger presented by the methyl nitrate
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In the solid state there are weak interactions between the O and N atoms of different molecules (see figure).
1383: 208: 171: 229: 1140:"Reaction of hydroxymethyl radicals with oxygen, nitric oxide, and nitrogen dioxide at room temperature" 1388: 647: 776: 757: 246: 1180:
Basic Chemistry of Explosives and Hazards of Home-Made Explosives and Chemical Precursors Handbook
1378: 1393: 761: 666: 1211:. Köhler, Josef., Homburg, Axel. (10., vollst. überarb. Aufl ed.). Weinheim: Wiley-VCH. 1072: 765: 732: 525: 75: 756:
The structure of methyl nitrate has been studied experimentally in the gas phase (combined
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Methyl nitrate can be produced on a laboratory or industrial scale either through the
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Friedel, Robert (2021). "Improvised Explosive Device Clearance Good Practice Guide".
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Vom griechischen Feuer zum Dynamit : eine Kulturgeschichte der Explosivstoffe
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Pagsberg, Palle; Munk, Jette; Anastasi, Christopher; Simpson, Victoria J. (1989).
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Table 1: Structural parameters of methyl nitrate Bond lengths in Å , angles in °
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According to A. Stettbacher, the substance was used as a combustible during the
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Solid-state structure of methyl nitrate determined by X-ray diffraction
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Except where otherwise noted, data are given for materials in their
782: 721: 533: 612:. The second procedure is essentially identical to that of making 132: 717: 360: 184: 1329: 983: 771: 712:("fireworks book") of about 1420 (the oldest technical text in 609: 917: 678: 497: 122: 234: 1137: 1099:
Shi, Jichun; Wallington, Timothy J.; Kaiser, E. W. (1993).
947: 669:, which prevents it from being stored or handled safely. 385:
64.6 °C (148.3 °F; 337.8 K) (explodes)
654:. The sensitivity of methyl nitrate to initiation by 775:
Gas phase structure of methyl nitrate determined by
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is among the greatest known, with even a number one
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of a mixture of methanol and nitric acid, or by the
1098: 677:As well as being an explosive, methyl nitrate is 1370: 516:. It is a colourless explosive volatile liquid. 196: 108: 1293: 1204: 375:−82.3 °C (−116.1 °F; 190.8 K) 1043:Fichter, Fr.; Metz, Fritz (January 1935). . 1278: 1246:(in German) (2. Auflage ed.). Berlin: 1042: 918:Meyer, R.; Köhler, J.; Homberg, A. (2007). 249: 174: 152: 1019: 1001: 216: 87:nitric acid methyl ester, nitrooxymethane 927:(6th ed.). Wiley-VCH. p. 212. 781: 770: 764:, GED/MW) and in the crystalline state ( 1243:Sprengstoffe, Treibmittel, Pyrotechnika 1176: 990:Angewandte Chemie International Edition 913: 911: 909: 894: 892: 633: 245: 1371: 902:(64th ed.). 1983. pp. C–376. 165: 900:CRC Handbook of Chemistry and Physics 727:An extract of the text from the 1420 277:Key: LRMHVVPPGGOAJQ-UHFFFAOYSA-N 1300:. Hamburg: E.S. Mittler & Sohn. 1240:Koch, Ernst-Christian (2019-06-17). 1239: 979: 977: 948:Black, A. P.; Babers, F. H. (1939). 906: 889: 681:and causes headaches when inhaled. 287:Key: LRMHVVPPGGOAJQ-UHFFFAOYAP 187: 13: 55: 46: 14: 1405: 1350: 1144:The Journal of Physical Chemistry 1105:The Journal of Physical Chemistry 974: 459: 33: 1322: 1287: 1272: 1233: 455:(at 25 °C , 100 kPa). 274:InChI=1S/CH3NO3/c1-5-2(3)4/h1H3 1198: 1170: 1131: 1092: 1036: 941: 638:Methyl nitrate is a sensitive 432:Occupational safety and health 284:InChI=1/CH3NO3/c1-5-2(3)4/h1H3 1: 882: 751: 604:of methanol by a mixture of 519: 7: 42: 10: 1410: 969:, vol. 2, p. 412 731:is as follows (written in 684: 524:It can be produced by the 420:6300 m s at ρ=1.217 g cm 15: 1283:. Rascher Verlag, Zürich. 1057:10.1002/hlca.193501801137 801: 672: 648:ethylene glycol dinitrate 449: 429: 424: 389: 347:77.04 g/mol 316: 296: 261: 92: 84: 74: 69: 41: 32: 1281:Schieß- und Sprengstoffe 1279:Stettbacher, A. (1948). 777:gas electron diffraction 758:gas-electron diffraction 16:Not to be confused with 1330:"www.feuerwerkbuch.de" 1294:Gartz, Jochen (2007). 1205:Meyer, Rudolf (2008). 1045:Helvetica Chimica Acta 1003:10.1002/anie.201911300 787: 779: 768:, XRD) (see Table 1). 762:microwave spectroscopy 749: 741: 445:Toxic, High Explosive 60: 51: 785: 774: 745: 737: 733:Early New High German 720:and later printed in 697:. This mixture would 59: 50: 1334:www.feuerwerkbuch.de 634:Explosive properties 564:A newer method uses 406:Friction sensitivity 1384:Explosive chemicals 1156:10.1021/j100350a028 1117:10.1021/j100125a016 996:(51): 18557–18561. 795: 628:di-tert-butyl ether 416:Detonation velocity 365:1.203 g/cm, liquid 29: 793: 788: 780: 482:Infobox references 61: 52: 27: 1389:Liquid explosives 1307:978-3-8132-0867-2 1257:978-3-11-055784-8 1218:978-3-527-32009-7 1150:(13): 5162–5165. 1111:(23): 6184–6192. 967:Collected Volumes 955:Organic Syntheses 934:978-3-527-31656-4 880: 879: 766:X-ray diffraction 716:, handwritten in 490:Chemical compound 488: 487: 396:Shock sensitivity 230:CompTox Dashboard 134:Interactive image 65: 64: 1401: 1365: 1358:"Methyl nitrate" 1344: 1343: 1341: 1340: 1326: 1320: 1319: 1291: 1285: 1284: 1276: 1270: 1269: 1237: 1231: 1230: 1202: 1196: 1195: 1193: 1191: 1185: 1174: 1168: 1167: 1135: 1129: 1128: 1096: 1090: 1089: 1083: 1078: 1076: 1068: 1051:(1): 1005–1007. 1040: 1034: 1033: 1023: 1005: 981: 972: 970: 963: 950:"Methyl nitrate" 945: 939: 938: 926: 915: 904: 903: 896: 796: 792: 506:chemical formula 472: 466: 463: 462: 324:Chemical formula 254: 253: 238: 236: 220: 200: 189: 178: 167: 156: 136: 112: 43: 37: 30: 26: 1409: 1408: 1404: 1403: 1402: 1400: 1399: 1398: 1369: 1368: 1356: 1353: 1348: 1347: 1338: 1336: 1328: 1327: 1323: 1308: 1292: 1288: 1277: 1273: 1258: 1238: 1234: 1219: 1203: 1199: 1189: 1187: 1183: 1175: 1171: 1136: 1132: 1097: 1093: 1081: 1079: 1070: 1069: 1041: 1037: 982: 975: 965: 946: 942: 935: 924: 916: 907: 898: 897: 890: 885: 870: 866: 841: 754: 714:German language 687: 675: 636: 591: 587: 583: 579: 559: 555: 551: 547: 543: 522: 515: 511: 491: 484: 479: 478: 477:  ?) 468: 464: 460: 456: 442: 390:Explosive data 336: 332: 326: 312: 309: 304: 303: 292: 289: 288: 285: 279: 278: 275: 269: 268: 257: 239: 232: 223: 203: 190: 159: 139: 126: 115: 102: 88: 80: 28:Methyl nitrate 25: 12: 11: 5: 1407: 1397: 1396: 1391: 1386: 1381: 1379:Alkyl nitrates 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798: 797: 791: 784: 778: 773: 769: 767: 763: 759: 748: 744: 740: 736: 734: 730: 729:Feuerwerkbuch 725: 723: 719: 715: 711: 710:Feuerwerkbuch 707: 702: 700: 696: 692: 682: 680: 670: 668: 663: 661: 657: 653: 649: 645: 644:nitroglycerin 641: 631: 629: 625: 620: 617: 615: 614:nitroglycerin 611: 607: 603: 599: 575: 574: 573: 571: 567: 566:methyl iodide 539: 538: 537: 535: 531: 527: 517: 507: 503: 499: 495: 483: 476: 471: 454: 448: 444: 439: 438: 434: 433: 428: 423: 419: 417: 414: 413: 409: 407: 404: 403: 399: 397: 394: 393: 388: 384: 382: 381:Boiling point 379: 378: 374: 372: 371:Melting point 369: 368: 364: 362: 359: 358: 354: 351: 350: 346: 344: 341: 340: 328: 325: 321: 320: 315: 306: 305: 302: 295: 281: 271: 270: 267: 260: 252: 248: 247:DTXSID4073205 244: 243: 241: 231: 227: 226: 219: 215: 214: 212: 210: 207: 206: 199: 195: 194: 192: 186: 182: 181: 177: 173: 170: 168: 166:ECHA InfoCard 163: 162: 155: 151: 150: 148: 146: 143: 142: 135: 131: 130: 128: 124: 119: 118: 111: 107: 106: 104: 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Retrieved 1333: 1324: 1296: 1289: 1280: 1274: 1242: 1235: 1207: 1200: 1188:. Retrieved 1179: 1172: 1147: 1143: 1133: 1108: 1104: 1094: 1073:cite journal 1048: 1044: 1038: 993: 989: 966: 959: 953: 943: 920: 899: 789: 755: 746: 743:Translated: 742: 738: 728: 726: 709: 703: 695:World War II 691:Nazi Germany 688: 676: 664: 660:blasting cap 650:, and other 637: 624:chloroethane 621: 618: 598:distillation 595: 563: 526:condensation 523: 504:and has the 493: 492: 441:Main hazards 430: 93:Identifiers 85:Other names 18:nitromethane 530:nitric acid 502:nitric acid 435:(OHS/OSH): 352:Appearance 317:Properties 172:100.009.039 1373:Categories 1339:2020-06-15 1266:1107346317 1248:De Gruyter 1082:|url= 921:Explosives 883:References 799:Parameter 667:volatility 656:detonation 343:Molar mass 218:LAD9RT85ES 145:ChemSpider 121:3D model ( 100:CAS Number 76:IUPAC name 1316:153884719 1227:244068971 1164:0022-3654 1125:0022-3654 1065:0018-019X 1012:1433-7851 876:131.4(4) 873:128.6(1) 858:113.6(3) 855:113.3(1) 847:1.205(1) 844:1.204(1) 833:1.403(2) 830:1.388(1) 822:1.425(3) 819:1.451(1) 752:Structure 699:evaporate 640:explosive 602:nitration 520:Synthesis 1030:31573130 869:terminal 865:terminal 840:terminal 722:Augsburg 606:sulfuric 580:I + AgNO 544:OH + HNO 534:methanol 425:Hazards 110:598-58-3 1364:. NIST. 1362:Webbook 1084:value ( 1021:6916544 811:GED/MW 718:Dresden 693:during 685:History 475:what is 473: ( 361:Density 355:Liquid 337: 185:PubChem 1314:  1304:  1264:  1254:  1225:  1215:  1190:29 May 1162:  1123:  1080:Check 1063:  1028:  1018:  1010:  931:  852:C–O–N 673:Safety 610:vapour 470:verify 467:  410:High 400:High 308:(=O)OC 301:SMILES 70:Names 1184:(PDF) 925:(PDF) 827:N–OC 679:toxic 592:+ AgI 498:ester 266:InChI 198:11724 154:11231 123:JSmol 1312:OCLC 1302:ISBN 1262:OCLC 1252:ISBN 1223:OCLC 1213:ISBN 1192:2024 1160:ISSN 1121:ISSN 1086:help 1061:ISSN 1026:PMID 1008:ISSN 962:: 64 929:ISBN 867:-N-O 816:C–O 808:XRD 760:and 584:→ CH 568:and 548:→ CH 532:and 209:UNII 1152:doi 1113:doi 1053:doi 1016:PMC 998:doi 838:N–O 735:): 724:). 626:or 556:+ H 528:of 500:of 235:EPA 188:CID 20:or 1375:: 1360:. 1332:. 1310:. 1260:. 1250:. 1221:. 1158:. 1148:93 1146:. 1142:. 1119:. 1109:97 1107:. 1103:. 1077:: 1075:}} 1071:{{ 1059:. 1049:18 1024:. 1014:. 1006:. 994:58 992:. 988:. 976:^ 964:; 960:19 958:. 952:. 908:^ 891:^ 646:, 588:NO 576:CH 572:: 552:NO 540:CH 536:: 512:NO 508:CH 333:NO 329:CH 1342:. 1318:. 1268:. 1229:. 1194:. 1166:. 1154:: 1127:. 1115:: 1088:) 1067:. 1055:: 1032:. 1000:: 971:. 937:. 863:O 590:3 586:3 582:3 578:3 560:O 558:2 554:3 550:3 546:3 542:3 514:3 510:3 465:Y 335:3 331:3 237:) 233:( 125:) 24:.

Index

nitromethane
methyl nitrite
Methyl nitrate


IUPAC name
CAS Number
598-58-3
JSmol
Interactive image
ChemSpider
11231
ECHA InfoCard
100.009.039
Edit this at Wikidata
PubChem
11724
UNII
LAD9RT85ES
CompTox Dashboard
DTXSID4073205
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Density
Melting point
Boiling point
Shock sensitivity

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