Toluene Toluidine

Attempts to use the reagent for the conversion of carboxylic acids into amides were not promising. In the presence of aluminum chloride (2 equiv.) the reagent reacts with an aromatic hydrocarbon with introduction of an amino group, but yields are very low benzene - aniline (28%) toluene - toluidine (50%), o m p = 51 13 36. ... 

Benzene Bromomethane 2-Butanone 2-Butoxyethanol Carbon disulfide 2-Chloroethanol Chloromethane Cresol(s) Cyclohexanol Cyclohexanone Dimethylformanude Dimethylsulfoxide 1,4-Dioxane 2-Ethoxyethanol Ethylbenzene Ethyl formate Ethylene glycol n-Hexane 2-Hexanone Methanol 2-Methoxyethanol Methyl formate Nitrobenzene Nitrotoluene(s) Phenol iso-Propyl benzene n-Propanol (ftom ACGIH) 1.1.2.2- Tetrachloroethane Tetrachloroethene Tetrachloromethane Toluene Toluidine(s) 1.1.2- Trichloroethane Trichloromethane Xylene(s)... 

It is prepared by the direct nitration of toluene as a 50-60% component of the mixture of isomers. Used for the preparation of o-toluidine. 

Prepared by mononilrating toluene, as a 40% constituent of the mixture of isomers. It is reduced to p-toluidine with iron and hydrochloric acid. 

The Hquid is basically a methacrylate monomer having a suitable inhibitor to ensure adequate shelf life. A/Ai -Dimethyl-/)-toluidine [99-97-8] is probably the most common polymerization accelerator although A/A/-bis(2-hydroxyethyl)- -toluidine and/or a sulfinate salt, eg, sodium -toluene sulfinate [873-55-2], also maybe used. 

After the addition of 2 1. of water, the mixture is steam-distilled as long as any oil comes over. The crude, heavy, yellow oil is separated and washed with two 200-cc. portions of 10 per cent sodium hydroxide, once with 100 cc. of water, twice with 150-cc. portions of concentrated sulfuric acid, and finally with 100 cc. of 5 per cent, sodium carbonate solution. It is dried with about 5 g. of calcium chloride, filtered through glass wool, and distilled using a long air condenser. Most of the product boils at i8o-i83°/75o mm. The yield of pure colorless material, b.p. i83°/76o mm., is 125-135 g. (36-39 per cent of the theoretical amount, based on the amount of -toluidine originally used, or 54-59 per cent based on the amount of 3-bromo-4-amino-toluene). 

Toluene-2,4-diammonium sulphate (4-methyl-m-phenylenediamine sulphate) o-Toluidine... 

Toluene-2,6-di isocyanate p-Toluene sulphonic acid o-Toluidine... 

Tokyo Kasei Kogyo Co., Ltd. (TKK), See Tokyo Chemical hidustry Co. Ltd. (Japan), 189 Tokyo Olika Kogyo Co., Ltd., 189 Toluene, 129 Toluene-2,4-dianiine, 130 Toluene 2,4-diisocyanate, 130 Toluene sulfonic acid, 130 o-Tolidiiie, 129 o-Toluidiiie, 130 Toluidines, 130... 

Toluene from Toluidine.—It is often desirable to obtain tbe hydiocarbon from the base. The process of diazotisntion offers the only convenient method. The diazonium salt may be reduced by alcohol (Reaction 1, p. 162) or, as in the piesent instance, by sodium stannite. Less direct methods are the con-veision of the diazonium compound into (i) the hydrazine (see p. 174), (2) the acid and distillation with lime (p. 200), (3) the halogen derivative and reduction with sodium amalgam, 01, finally (4) the phenol and distillation with zinc dust. 

Tartaric acid, 114 Terephthalic acid, i7r Tetrabromocresol, 165 7 hiocarbamide, 128 Thiocarbanilamide, 159 Thiocarbanilide, 159 Thiourea, 128 /i-Tolyl bromide, 167 / Tolyl chloride, 165 /-Tolyl cyanide, 169 Tolyliodochloride, 169 Toluene from toluidine, 163 / Toluic acid, 170 Tribromophenol, 180 Trichloracetic acid, 99 Trimethylxanthine, 131 l rinitrophenol, 185 Triphenylguanidine, ito Triphenylmetbane, 2 4 J schugac s hydroxyl method, 223 Tube furnace, 23 Tyrosine, 133... 

While the direct halogenation of toluene gives a mixture of isomers that is difficult to separate into the pure isomers, the isomeric o- and /r-nitrotoluenes 6a and 6b, formed by nitration, are easy to separate from each other. Thus reduction of the single o- or /j-nitrotoluene 6 to the o- or /j-toluidine 7a or 7b respectively, followed by conversion into the corresponding diazonium salt 8 and a subsequent Sandmeyer reaction leads to the pure o- or /j-halotoluene 9. 

Preparation of Intermediate Compound 2-Methyl-3-o-Tolyl-6-Sulfamyl-7-Chloro-4(3H)-Quinazoiinone Set up a 5-liter 3-necked flask fitted with a stirrer, condenser and a drying tube. To a stirred mixture of 100 g (0.342 mol) of powdered 4-chloro-5-sulfamyl-N-acetylanthranilic acid, 40.2 g (0.376 mol) of o-toluidine and 2.0 liters of dry toluene was added dropwise, over a period of 15 minutes, 21.7 ml (34.1 g) (0.248 mol) of phosphorus trichloride. The mixture was then refluxed for 10 hours. The solid turned somewhat gummy towards the latter part of the first hour. The mixture then became more free flowing as heating was continued. Let stand overnight. The yellow solid was filtered, washed with toluene and dried. The toluene filtrate was discarded. The dried solid was triturated with 1.5 liters of 10% sodium bicarbonate, filtered and the cake washed with water. The filtrate on acidification yielded 11.5 g of the starting acid. The damp product was dissolved in 4,5 liters of 95% ethanol and the solution treated with charcoal and filtered. On cooling filtrate yielded 69.5 g (55.5%) of the title compound, MP 271.5° to 274°C. 

Toluidine, nitrotoluene isomers, diaminotoluene, and dinitro-toluene isomers... 

The hydrogenation of toluene, aniline, /r-toluidine, and 4-tert-butylaniline was examined over catalyst M1273. The reaction profile for the reactions is shown in Figure 2. From this it can be seen that the order of reactivity is aniline > toluene > /Moluidinc > 4-fer f-butylaniline. The hydrogenation products were methylcyclohexane from toluene, cyclohexylamine from aniline, 4-methyl-cyclohexylamine (4-MCYA) from /Holuidine. and 4-feri-butylcyclohexylamine (4-tBuCYA) from 4-tert-butylaniline. At 50 % conversion the cis trans ratio of 4-MCYA was 2, while tBuCYA it was 1.6. 

Figure 2 Hydrogenation of aniline, toluene, p-toluidine, 4-tert-butylaniline, over M1273. Temperature 338 K and 2 barg hydrogen pressure.

---