Paraffins Nitro

The nitre paraffins (nitro methane am) nitmethane) became commercially available in the early 1440s. Several milhwn pounds arc produced annually by the vapor-phase reaction of propane and nitric acid ut elevated temperature ami pressure These compounds and ihcir derivatives find applications as fuels, solvents, and explosives. 

The main index headings for search other than the names of specific compounds are Paraffins nitration of Paraffins, nitro Paraffins, from nitration of— Paraffins, dinitro Hydrocaibons, nitration of Nitration of hydrocarbons Nitration of paraffins Petroleum, nitrogen compounds from Olefins, nitro derivatives and Acetylenes, nitro derivatives. These items are not mutually inclusive, e.g., references under Paraffins, nitration of are not necessarily to be found under Nitration of paraffins. In Chemical Abstracts collective index for 1937 to 1946, there are 19 entries under the first heading and 12 entries under the second only 10 are common to both lists. 

CH,),CHNO, -h HONO = (CH,),C(NO)NO, -h H,0 producing a blue solution. A tertiary nitro paraffin such as trimethylnitro-methane, (CH )jCNO, gives no reaction with nitrous acid. 

In addition to its water solubility poly(vinyl pyrrolidone) is soluble in a very wide range of materials, including aliphatic halogenated hydrocarbons (methylene dichloride, chloroform), many monohydric and polyhdric alcohols (methanol, ethanol, ethylene glycol), some ketones (acetyl acetone) and lactones (a-butyrolactone), lower aliphatic acids (glacial acetic acid) and the nitro-paraffins. The polymer is also compatible with a wide range of other synthetic polymers, with gums and with plasticisers. 

C. MEDINA. The crude methylenedi(nitro-formamide) is pressed dry on the filter, stirred into lOSml of formic acid, and the paste allowed to stand overnight. The next day the soln is filtered thru an acid-proof flit, the formic acid and w removed by codistn with xylene, and the crude MEDINA, which seps as a sand, filtered and dried over paraffin and NaOH in a vacuum yield 80—100% based on methylene diform-amide, mp 98—103°. The crude MEDINA is recrystd from 2-nitropropane or et chloride iso-Pr ale 9 1, mp 104-059 (Ref 11, p 54). This prepn is also covered in Ref 20... 

H. Aaronson, Study of Explosives Derived From Nitro paraffins", PATR 1125 (1941), p 4 Table II... 

K chlorate and aromatic hydrocarbons (such as naphthalene), and not more than 12% nitro-hydrocarbons (but no trinitro compds), the remainder consisting of paraffins, fatty oils, flour or other combustibles. It might also contain not more than 4% blasting gelatin. The prefixes Gesteins- and Wetter- were applied if the expls were intended for rock or coal mine use Ref Marshall, Diet (1920), 65... 

A series of nitrated and unsaturated hydrocarbons. The base molecule for nomenclature purposes is usually called the "ethylene series1 because the first member is ethylene, C2H4 hence a molecular type CnH(2n-x)Nx02x s derived. Other compds in the series are named after corresponding paraffins by adding to the stem ene or ylene such as 1-nitro propylene, C3H5NO2. Olefms with two conjugeted double bonds are called dienes , such as butadiene. 

Sterlington, Louisiana explosion at a nitro-paraffin plant. 

As early as 1910, Franchimont[16] observed that primary nitramines (and nitro-paraffins) react with formaldehyde and secondary amines (e.g. piperidine). The formation of aminomethylnitramines (IV) then occurs ... 

Thus, if there is a need to reduce the melting point of a nitro compound, e.g. picric acid, other nitro compounds are added to form an eutectic mixture to decrease the sensitiveness of picric acid to mechanical impact it is mixed with paraffin. 

H-R. Fee J-D. Ferguson, USP 3356544 (1967) CA 68, 5l 492y(1968) [Blasting compns are described consisting of aq slurries of inorg oxidizer salt (such as AN or NaNOa), a nitro-paraffin sensitizer contg 1—3 C atoms, and... 

To eliminate the influence of internal hydrogen bonds, nitro-paraffins and their hydroxyl derivatives have been examined in solution in carbon tetrachloride or cyclohexane. In this instance two vQH bands were observed strong bands due to free OH groups with frequencies 3774-3636 cm-1 and weak ones of bonded OH groups with frequencies 3390-3176 cm"1. 

Nitroaminocompounds of the type (II) were also examined in suspension in paraffin oil. They contain NH groups which give rise to bands with frequencies 3030 and 1610 cm1. The r correspond to NH groups bonded with hydrogen bonds. The frequencies of the nitro group are lowered in all nitro niino compounds with an exception of the compound (IIa) which does not contain hydroxyl groups. This may be accounted for by the weakness of bifurcated hydrogen bonds. 

HMX HMX HMX HMX HMX HMX HMX HMX HMX HMX HMX HMX HNS NTO NTO/HMX NTO/HMX NTO/HMX PETN PETN PETN PETN PETN PETN PETN PETN PETN PETN RDX RDX RDX RDX RDX RDX RDX RDX RDX RDX RDX RDX RDX TATB/HMX Cariflex (thermoplastic elastomer) Hydroxy-terminated polybutadiene (polyurethane) Hydroxy-terminated polyester Kraton (block copolymer of styrene and ethylene-butylene) Nylon (polyamide) Polyester resin-styrene Polyethylene Polyurethane Poly(vinyl) alcohol Poly(vinyl) butyral resin Teflon (polytetrafluoroethylene) Viton (fluoroelastomer) Teflon (polytetrafluoroethylene) Cariflex (block copolymer of butadiene-styrene) Cariflex (block copolymer of butadiene-styrene) Estane (polyester polyurethane copolymer) Hytemp (thermoplastic elastomer) Butyl rubber with acetyl tributylcitrate Epoxy resin-diethylenetriamine Kraton (block copolymer of styrene and ethylene-butylene) Latex with bis-(2-ethylhexyl adipate) Nylon (polyamide) Polyester and styrene copolymer Poly(ethyl acrylate) with dibutyl phthalate Silicone rubber Viton (fluoroelastomer) Teflon (polytetrafluoroethylene) Epoxy ether Exon (polychlorotrifluoroethylene/vinylidine chloride) Hydroxy-terminated polybutadiene (polyurethane) Kel-F (polychlorotrifluoroethylene) Nylon (polyamide) Nylon and aluminium Nitro-fluoroalkyl epoxides Polyacrylate and paraffin Polyamide resin Polyisobutylene/Teflon (polytetrafluoroethylene) Polyester Polystyrene Teflon (polytetrafluoroethylene) Kraton (block copolymer of styrene and ethylene-butylene)... 

Alcohols, Nitrated, Preparation from nitro-paraffins by condensation with aldehydes in the presence of an alkaline catalysts is discussed by H.A.Aaronson in PATR 1125 (1941)... 

Claik Hawley( 1957),846-7 Aldehyde-Nitroparaffin Reactions. The reaction between an aldehyde and a nitro-paraffin usually proceeds as follows ... 

The lower members of the homologous series of 1. Alcohols 2. Aldehydes 3. Ketones 4. Acids 5. Esters 6. Phenols 7. Anhydrides 8. Amines 9. Nitriles 10. Polyhydroxy phenols 1. Polybasic acids and hydro-oxy acids. 2. Glycols, poly-hydric alcohols, polyhydroxy aldehydes and ketones (sugars) 3. Some amides, ammo acids, di-and polyamino compounds, amino alcohols 4. Sulphonic acids 5. Sulphinic acids 6. Salts 1. Acids 2. Phenols 3. Imides 4. Some primary and secondary nitro compounds oximes 5. Mercaptans and thiophenols 6. Sulphonic acids, sulphinic acids, sulphuric acids, and sul-phonamides 7. Some diketones and (3-keto esters 1. Primary amines 2. Secondary aliphatic and aryl-alkyl amines 3. Aliphatic and some aryl-alkyl tertiary amines 4. Hydrazines 1. Unsaturated hydrocarbons 2. Some poly-alkylated aromatic hydrocarbons 3. Alcohols 4. Aldehydes 5. Ketones 6. Esters 7. Anhydrides 8. Ethers and acetals 9. Lactones 10. Acyl halides 1. Saturated aliphatic hydrocarbons Cyclic paraffin hydrocarbons 3. Aromatic hydrocarbons 4. Halogen derivatives of 1, 2 and 3 5. Diaryl ethers 1. Nitro compounds (tertiary) 2. Amides and derivatives of aldehydes and ketones 3. Nitriles 4. Negatively substituted amines 5. Nitroso, azo, hy-drazo, and other intermediate reduction products of nitro com-pounds 6. Sulphones, sul-phonamides of secondary amines, sulphides, sulphates and other Sulphur compounds... 

Nitro-paraffins may be primary, secondary or tertiary —CH,.NO primary >CH.NO secondary and >C.NOto tertiary. 

If we assume that it is possible to reduce an aliphatic nitro compound to the corresponding nitroso compound, the possibility of a simultaneous isomerisation to an oxime has to be kept in mind. It is known from the reduction of primary and secondary nitro paraffins by stannous chloride1121, that the reduction does not proceed to form amines, which could be explained by a rapid isomerisation of the adsorbed intermediate to an oxime. 

Nitro-1-butene, CH3.CH2C (N02) CH2, liq, bp 60.5° at 50mm(Refs 4 8), volatility vap press are given by Redemann et al(Ref 6) during the prepn of polynitro paraffins, Bahner Kite (Ref 7) found that metallic Na added to an equi-molar mixt of (CH3)2CH.N02 2-nitro-l -butene at 8° caused a violent reaction mild expln l-Nitro-2-butene(irons), CH3.CH CH.-... 

A continuous method of manufg nitro-paraffins developed by Commercial Solvents Corp) 36)N,A.P.Nilsson, USP 2737522 (1956) CA 50, 6796 (1956) (An improved continuous method for production of liquid... 

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