White fuming nitric acid

A. Acetone cyanohydrin nitrate. White fuming nitric acid (106 ml., 158 g., 2.3 moles) (Note 1) is added dropwise to 380 ml. (408 g., 4.00 moles) of acetic anhydride at 3-5° contained in a 2-1. three-necked flask fitted with a stirrer, a thermometer, and a dropping funnel and immersed in an ice bath. After the addition, which requires 45 minutes, the mixture is stirred at 5° for 15 minutes (Note 2). Acetone cyanohydrin (92 ml., 85 g., 1.00 mole) (Note 3) is added dropwise to the mixture at 5-10° over a 45-minute period. After the addition, the ice bath is removed and the mixture is allowed to warm to room temperature and is stirred there for 30 minutes. It is then poured into 600 g. of ice... 

The reaction conditions necessary to obtain a good yield of the title compound (a difficult isomer), and to avoid hazards during the nitration of resorcinol, are critical and strict adherence to those specified is essential. The necessary 80% white fuming nitric acid must be completely free from oxides of nitrogen and nitrous acid, and procedures for this are detailed. Then the temperature dining addition of the diacetate must be kept between -10 and 0°C by regulating the rate of addition. The alternative use of 80% sulfuric acid as solvent for the 80% nitric acid (5 equiv.) is preferred as more reliable, but both methods have led to violent exothermic decomposition, accompanied by fume-off, after an induction period. In any event, the explosive 2,4,6-trinitroresorcinol ( styphnic acid ) is produced as a by-product. 

In contact with white fuming nitric acid, ignition delays for tributylamine, tripropylamine and triethylamine were less than those of the corresponding dialkylamines, and under good mixing conditions, butylamine did not ignite [1]. Triethylamine ignites on contact with the cone, acid [2],... 

However JATO units based on liq propellants have also been used for example the Tonka fuels used with white fuming nitric acid (Ref 1). Tonka fuels are mixtures of aniline, monomethylaniline, dime thylaniline,... 

Fuming Nitric Acids. There are WFNA (white fuming nitric acid) and RFNA (red fuming nitric acid). They are described under Nitric Acid and in CondChemDict (1961), p 800 R (1971), 618-R... 

IWFNA (inhibited white fuming nitric acid) 97.5% HN03-1.5% H2O-0.3% N.204-0.7% HF Lox (L02) Liquid oxygen, 02... 

Nitric Acid and Nitrates. The use of nitric acid as a major component in liquid oxidizers dates back to at least World War II when it was used in a mixture with oleum (88 wt. % white fuming nitric acid and 12 wt. % oleum) and was denoted as mixed acid. In later years its use as white fuming nitric acid (WFNA) and inhibited white fuming nitric acid (IWFNA) developed because of its higher performance capabilities in these forms. These acids are fairly pure nitric acid WFNA contains a maximum of 2 wt. % H20 and 0.5 wt. % N02 IWFNA addi-... 

N 13.16% wh ndls (from ale or glac acet ac), mp 160.5—162° was prepd by adding portion-wise benzhydrol to white fuming nitric acid held at 28 —30°. The dk red soln was allowed to stand 5 hrs, then poured into chopped ice water. The mixt was filtered and the crude product recrystallized 4 times from glac acet ac and an addnl time from a large vol of alcohol (Ref 3a)... 

It has been used as a solvent and as an intermediate in the manuf of chemicals used in the expl industry and of synthetic rubber (Ref 4). During WWII, acetal(as well as acetaldehyde) was used in Germany as hyper-gollic fuel in liquid rocket propellants in conjunction with red or white fuming nitric acid which served as an oxidizer. Acetal was later replaced by ca te ch o 1( Bren zc ate chin or Brenzol in Ger)(Ref 10)... 

The compressibilities specific heat ratios of some rocket propellants liquids such as hydrazine, JP-3, JP-4 WFNA (white fuming nitric acid)] are reported by Kretschmar (Ref 3)... 

W(Pulver) an old Austrian black powder WFN or WFNA white fuming nitric acid... 

Acute inhalation toxicity of nitrogen dioxide, red fuming nitric acid, and white fuming nitric acid. Arch. Ind. Hyg. Occup. Med. 10 418-422. 

---