Nitro, acids glycerol

Violent reaction or ignition under the proper conditions with acetone + tert-butylamine, alcohols + nitric acid, aluminum carbide, ammonia + sulfuric acid, antimony, coal + peroxomonosulfuric acid, dichloromethylsilane, dimethyl sulfoxide, ethanol + sulfuric acid, glycerol, concentrated hydrofluoric acid, hydrogen peroxide, hydrogen trisulfide, hydroxylamine, carhon, organic nitro... 

Alizarine Blue. 5 Dihydroxynaphtho[2,2 /]quin-oiine-7,l2 dione 7.8-dihydroxy-5,6-phthaly[quinoline Alizarin Blue R C.I. 67410- C 7H9N04 mol wt 291-25. C 70,10%, H 3.12%, N 4.81%, O 21,97%. Prepn from 3-nitro-alizarin, glycerol, and coned sulfuric acid Auerbach, J. 

Place 24 ml. (24 5 g.) of aniline, 13 ml. (15 5 g.) of nitro-benzene,t and 62 ml. (75 g.) of the anhydrous glycerol in the flask and mix thoroughly. (If the glycerol is still warm from the dehydration, cool the mixture in water.) Now add slowly 36 ml. (66 g.) of concentrated sulphuric acid, shaking the mixture thoroughly during the addition. The mixture at first... 

Hydroxyquinoline ( oxine ). The technique adopted in this preparation is based upon the fact that, in general, the reactants glycerol, amine, nitro compound and sulphuric acid can be mixed with temperature control, and then maintained at any convenient temperature below 120° without any appreciable chemical reaction taking place. A pre-mix of the amine, glycerol and sulphuric acid, maintained at a temperature which keeps it fluid (60-90°), is added in portions to a reaction vessel containiug the nitro compound and warmed with stirring to 140-170° at which temperature the Skraup reaction takes place. 

Removal of the nitro group results in an alteration of antimicrobial spectrum leading to a series of antifungal agents. For example, reaction of 2,4-dichloroacetophenone with glycerol and tosic acid leads to dioxolane Under bromin-... 

Primaquine Primaquine, 8-[(4-amino-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.4), is made from 6-methoxy-8-nitroquinoline (37.1.2.1), which is synthesized in a Skraup reaction from 4-methoxy-2-nitroaniline and glycerol in the presence of sulfuric acid. The nitro group in this compound is reduced to make 6-methoxy-8-aminoquinoline (37.1.2.2). Alkylating the amino group with 4-bromo-l-phthalimidopentane gives 8-[(4-phthalimido-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.3), the hydrazi-nolysis of which removes the phthalimide protection, giving primaqnine [28,29]. 

Sometimes the amine can be dispensed with, and the corresponding nitro-body used alone. It is reduced by the hydrogen arising in the reaction. Of technical interest is the fact that /J-nitro-alizarin on heating with glycerol and sulphuric acid yields a blue dye—Alizarin Blue. (B., 16, 445 29, 708 A., 201, 333.)... 

An important use of the traditional Skraup synthesis is to make 6-methoxy-8-nitroquinoline from an aromatic amine with only one free ortho position, glycerol, the usual concentrated sulfuric acid, and the oxidant arsenic pentoxide. Though the reported procedure uses 588 grams of As2Os, which might disconcert many chemists, it works well and the product can be turned into other quinolines by reduction of the nitro group, diazotization, and nucleophilic substitution (Chapter 23). 

An oxidant. Combusdble when exposed to heat and flame. Moderate explosion hazard when exposed to heat or flame. Explosive reacdon with solid or concentrated alkali + heat (e.g., sodium hydroxide or potassium hydroxide), aluminum chloride + phenol (at 120°C), aniline + glycerol + sulfuric acid, nitric + sulfuric acid + heat. Forms explosive mixmres with aluminum chloride, oxidants (e.g., fluorodinitromethane, uranium perchlorate, tetranitromethane, sodium chlorate, nitric acid, nitric acid + water, peroxodisulfuric acid, dinitrogen tetraoxide), phosphorus pentachloride, potassium, sulfuric acid. Reacts violendy with aniline + glycerin, N2O, AgC104. To fight fire, use water, foam, CO2, dry chemical. Incompadble with potassium hydroxide. When heated to decomposidon it emits toxic flames of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS. 

Hydrocyanic acid is miscible in all proportions with alcohol, ether, glycerol, chloroform, benzene, tricresyl phosphate, etc. It does not dissolve nitro-cellulose, but cellulose acetate and the other cellulose esters are soluble. Gums, rubber and gelatin are not dissolved. Carbon dioxide and hydrogen sulphide are slightly soluble and sulphur dioxide is soluble in all proportions. ... 

Gun Cotton.—As nitric acid esters of poly-hydroxy alcohols, the two important explosives nitro glycerol and gun cotton are exactly analogous not only in character but also in the fact that each is the... 

A mixture of 2-chloro-5-nitro-benzoic acid and amine derivatives in glycerol was stirred with heat adding potassium carbonate. 

Skraup reaction The reaction between glycerol, sulphuric acid, a primary aromatic amine and an aromatic nitro compound to give a quinoline. 

From alizarin there can be prepared, further, by nitration, the a- or /J-nitro-alizarin, and from this, by reduction, the corresponding amido-alizarin. From (i-nitro- and amido-alizariu, by heating with glycerol and sulphuric acid, the important Alizarin Blue is obtained. Further, by the action of fuming sulphuric add on alizarin there is obtained a tetraoxyanthraquinone (Bordeaux), etc. 

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