Aurelius (Hive Addict) 06-11-03 03:14 No 438964 |
Compilation of Nitroethane Syntheses (Rated as: excellent) |
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Compilation of Nitroethane Syntheses All Methods #1-23 have basic abstracts, links and information to be found in the thread beginning with this post: Post 103078 (rev drone: "What can be done to improve the performance of clandestine nitroethane synth?", Chemistry Discourse) OR AT: ../rhodium /nitroet Additional information links and posts will be listed underneath its respective synthesis as they become available. Some safety information regarding Nitroethane: Nitroethane, Ethyl nitrate and Ethyl Nitrite Post 392844 (Rhodium: "Nitroethane from ethanol", Chemistry Discourse) Method 1: from sodium ethyl sulfate and a metal nitrite patent CH74333 Text for patent above: Post 436963 (Organikum: "Patents on nitroethane - translation", Chemistry Discourse) Method 2: from diethyl sulfate and sodium nitrite patent CH75523 Text for patent above: Post 437812 (jimwig: "No 436362 nitroethane revisited again too...", Chemistry Discourse) Experiences with this method: Post 384841 (roger2003: "Method 2: from diethyl sulfate and sodium nitrite ...", Chemistry Discourse) Prep’ing dialkylsulfates: Experiences with preparations: Post 233762 (Antoncho: "Kitchen nitroalkane success!", Chemistry Discourse) Post 251119 (Bandil: "Nitroethane ala Antoncho succes", Novel Discourse) Post 399668 (Antoncho: "Some problems with nitroethane synth...", Methods Discourse) Method 3: from ethyl bromide (iodide) and sodium nitrite (dmf) Method 4 : from ethyl halide and silver nitrite Method 5: oxidation of ethyl amine with peracids (m-perbenzoicacid) See Method 21: Method 6: oxidation of ethyl amine with potassium permanganate See Method 21: http://www.orgsyn.org/orgsyn/prep.asp?pr Method 7: destructive distillation of alpha-bromopropionic acid with sodium nitrite Synthesis of alpha-bromopropionic acid http://www.orgsyn.org/orgsyn/orgsyn/prep Method 8: oxidation of ethyl amine to nitroethane with dimethyldioxirane Method 9: isomerization of ethyl nitrite to nitroethane over asbestos catalyst Method 10: ethyl bromide, DMSO, NaNO2 and phloroglucinol dihydrate Preparation of Phloroglucinol Post 385985 (lugh: "Phlorglucinol synthesis details", Chemistry Discourse) Post 331397 (hypo: "Phloroglucinol and pyrocatechol from phenol", Novel Discourse) Post 199920 (obituary: "synth of phloroglucinol", Methods Discourse) Other nitrite scavenging possibilities: Post 276855 (starlight: "phloroglucinol / catechol / pyrogallol", Chemistry Discourse) Method 11: 3-chloropropionic acid sodium salt, and NaNO2 Originally found by WizardX, but Joyman posted the method details Post 238127 (joyman: "Re: What can be done to improve the performance of clandestine nitroethane synth?", Chemistry Discourse) The orginal article on which this method is based: http://www.orgsyn.org/orgsyn/prep.asp?pr Another modification of the method above: Post 236612 (malvaxman: "Nice nitroethane synth by WizardX", Methods Discourse) Method 12: most complicated synth Method 13: electrochemical oxidation ---- not possible by method below Method 14, 15 and 16: Vapor Phase nitration of propane, ethane and ethanol respectively Other vapor-phase nitration references: Post 396687 (Aurelius: "Other Patents", Chemistry Discourse) Post 398745 (Aurelius: "Some Reference Materials in the Compilation", Chemistry Discourse) Patent US4431842 Text of the patent above: Post 396685 (Aurelius: "Patent References US patent", Chemistry Discourse) Method 17: Distillation of alpha-bromopropionic acids with NaNO2 in the presence of Magnesium Sulfate in DMSO Patent US4319059 Text for this patent may be found here: Post 396684 (Aurelius: "Patent References US patent 4319059", Chemistry Discourse) Patent US4431842 Text of the patent above: Post 396685 (Aurelius: "Patent References US patent", Chemistry Discourse) Method 18: Oxidation of alanine with permanganate followed by decarboxylation Method 19: Reduction of acetaldehyde oxime and oxidation of the product Method 20: reduction of nitroethene to nitroethane using 2-phenylbenzimidazoline Method 21: Oxidation of ethyl amine Nitroethane via Permanganate (Buffered with MgSO4 and not) oxidation of ethyl amine: http://www.orgsyn.org/orgsyn/prep.asp?pr The above is just like Method 6 Oxidation via H2O2: Oxidation with Peracids acid (Buffered and not): The above is just like Method 5 Oxidation with THBP over CrS-2: Oxidation with DMDO: Each of the oxidations just listed can be found at this link: Post 398745 (Aurelius: "Some Reference Materials in the Compilation", Chemistry Discourse) Synthesis of Ethyl Amine: Ethyl amine from acetonitrile via Al/Hg: Post 2813 (BrightStar: "Re: nitroethene", Chemistry Discourse) Method 22: Nitroethane from propyl nitrate J.B. Levy ; F.J. Adrian, J. Amer. Soc. 77, 2015 (1954) Method 23: Nitroethane from nitroethene (and nitroethanol) Nitroethane via nitroethene reduction with NaBH4: Post 216376 (slappy: "Re: Nitroethene Reduction to Nitroethane", Chemistry Discourse) Nitroethane via nitroethene reduction with Baker’s Yeast: Post 108516 (dormouse: "A new reducing agent for nitrostyrenes: bakers yeast! -Labrat", Novel Discourse) Synthesis of Nitroethene: Nitromethane, formaldehyde and ammonium acetatenot certain that nitroethanol isn’t formed instead Post 2716 (psyloxy: "nitroethene", Chemistry Discourse) Vapor-phase Nitromethane, formaldehyde over catalyst Post 216189 (halfapint: "Nitroethene Reduction to Nitroethane", Chemistry Discourse) Dehydration of Nitroethanol no method given, should be performed with H2SO4, H3PO4 or KHSO4 Synthesis of Nitroethanol: Nitromethane, formaldehyde in alkaline aqueous solution: Post 216189 (halfapint: "Nitroethene Reduction to Nitroethane", Chemistry Discourse) Method 24: Nitroethane from ethanol (doesn’t work as proposed in article 1) Proposed method: ../rhodium /alcohol Reality: ../rhodium/pdf /nitroalcohol. The first article shows the formation of nitroethane. However, the second article presents convincing evidence that ethyl nitrite is actually formed. Method 9 gives an option for ethyl nitrite to nitroethane- however, it is considered an industrial procedure. Method 25: Oxidation of acetaldoxime to nitroethane with Na perborate Post 435910 (Lego: "Oximes to nitro alkanes with sodium perborate", Chemistry Discourse) Method 26: Oxidation of acetaldoxime with Oxone in MeCN Post 435890 (Lego: "Oxidation of oximes to nitroalkanes", Chemistry Discourse) Method 27: Oxidation of acetaldoxime with peroxytrifluoroacetic acid J. Am. Chem. Soc., 1955, 77, 4557 Method 28: Oxidation of acetaldoxime with Urea-H2O2 complex in MeCN Tet. Lett, 1992, 33, 4835 Method 29: Oxidation of acetaldoxime with Benz-Mo in MeCN Synlett, 1996, 1093 Method 30: Direct Nitration of Ethane (alkanes) with Nitronium Hexafluorophosphate Post 471835 (pHarmacist: "Direct Nitration of Alkanes", Chemistry Discourse) Method 31: Ethyl Halide to Nitroethane w/PTC Post 474349 (Lego: "Nitroalkanes from bromoalkanes with PTC", Chemistry Discourse) References for various methods given above: Post 474663 (Rhodium: "original nitroethane literature", Methods Discourse) Act quickly or not at all. |
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