P-Aminophenol

Add 4 4 g. of recrystaUised -phenylhydroxylamine to a mixture of 20 ml. of concentrated sulphuric acid and 60 g. of ice contained in a 1 litre beaker cooled in a freezing mixture. Dilute the solution with 400 ml. of water, and boil until a sample, tested with dichromate solution, gives the smell of quinone and not of nitrosobenzene or nitrobenzene (ca. 10-15 minutes). Neutralise the cold reaction mixture with sodium bicarbonate, saturate with salt, extract twice with ether, and dry the ethereal extract with anhydrous magnesium or sodium sulphate. Distil off the ether p-aminophenol, m.p. 186°, remains. The yield is 4-3 g. 

Suspend 11 g. of p-aminophenol in 30 ml. of water contained in a 250 ml. beaker or conical flask and add 12 ml. of acetic anhydride. Stir (or shake) the mixture vigorously and warm on a water bath. The solid dissolves. After 10 minutes, cool, filter the solid acetyl derivative at the pump and wash with a little cold water. Recrystallise from hot water (about 75 ml.) and dry upon filter paper in the air. The yield of p-acetylaminophenol, m.p. 169° (1), is 14 g. 

Acid YeUow 23 (31), commonly known as Tartraziae, stiU maintains sales of nearly 0.5 million /yr ia the United States. It was first discovered ia 1884 and is made by coupling equimolar quantities of diazotized sulfarulic acid to 3-carboxy-l- -sulfophenyl)-5-pyrazolone. Other monoazopyrazolone dyes of commercial importance iaclude Acid YeUow 17 (32) (sulfarulic acid — l-(2,5-dichloro-4-sulfophenyl)-3-methyl-5-pyrazolone and Acid YeUow 40 [6372-96-9] (33) (Cl 18950) (p-aminophenol l-(4-chloro-2-sulfophenyl)-3-methyl-5-pyrazolone) foUowed by esterification of the phenoUc hydroxy group with -toluenesulfonyl chloride. 

ANILINE Total p-aminophenol in urine End of shift 50 mg/g creatinine Ns... 

Thus, acetylation of aniline affords acetanilide (20), an analgesic widely used in proprietary headache remedies. A similar transformation on p-aminophenol gives the analgesic, acetaminophen (21). It is of interest that the latter is also formed in vivo on administration of 21. An interesting preparation of this drug involves Schmidt rearrangement of the hydrazone (24) from p-liydroxyacetophenone. ... 

Paralyse, /. paralysis, paralysieren, v.t. paralyze, paramagnetisch, a. paramagnetic. Paramidophenol, n. p-aminophenol. Paramilchsaure, /. paralactic acid (d xtro-lactic acid). 

Phenylhydroxylamine rearranges in sulfuric acid to give mainly p-aminophenol. Industrial routes to this compound have been developed in which phenylhydroxylamine, formed by hydrogenation of nitrobenzene in sulfuric acid over platinum-on-carbon, is rearranged as it is formed. Conditions are adjusted so that the rate of rearran ment is high relative to the rate of hydrogenation of hydroxylamine to aniline (15,17,86). An easy way to obtain a favorable rate ratio is to carry out the reduction with about 1% DMSO present in the sulfuric acid (79,81). 

About 250 ml of a reaction mixture obtained by the electrolytic reduction of nitrobenzene in sulfuric acid solution and containing about 23 grams of p-aminophenol by assay is neutralized while at a temperature of 60° to 65°C, to a pH of 4.5 with calcium carbonate. The calcium sulfate precipitate which forms is filtered off, the precipitate washed with hot water at about 65°C and the filtrate and wash water then combined. The solution is then extracted twice with 25 ml portions of benzene and the aqueous phase is treated with 0.5 part by weight, for each part of p-aminophenol present, of activated carbon and the latter filtered off. The activated carbon is regenerated by treatment with hot dilute caustic followed by a hot dilute acid wash, and reused a minimum of three times. 

To the filtrate obtained, there are then added about 0.2 gram of sodium hydrosulfite or sodium sulfite and 15.0 grams of anhydrous sodium acetate in about 27 grams of acetic anhydride at 40°C. The reaction mixture formed is cooled to 8° to 10°C with stirring and held at this temperature for 60 minutes. A crystalline precipitate of about 27 grams of N-acetyl-p-aminophenol is obtained melting at 169°-171°C. This is equivalent to a yield of 85%. 

Example 1 65 grams of N-acetyl-p-aminophenol were slurried with 400 ml of water and cooled to 10°C. 125 ml of 20% sodium hydroxide were slowly added to the mixture with... 

Example 2 65 grams of sodium N-acetyl-p-aminophenol were slurried with 500 grams of dry benzene and 80 grams of acetyl salicoyl chloride added. The mixture was heated under reflux for four hours and filtered hot. The excess benzene was removed under vacuum and the crude acetyl salicyclic acid ester of N-acetyl-p-aminophenol crystallized from ethanol. 

Aminophenols (underivatized) o-aminophenol, p-aminophenol, and acetanilide 30 m DB-1701 column, 45-250° at 107min. 

I-A1ON0-2-NAPHIH0L-4-SULE0NIC acid, 11, 72 16, 91 17, 91 Aminonaphtholsulfonic acids, coupling to form azo dyes, 16,16 p-Aminophenol, 16, 39 Aminopiperole, 16, 6 /3-Ahinopropionic acid, 16, 1 4-Aminoveratrole, 16, 4 Ammonium dichromate, 16, 74 Ammonium formate, 17, 77 Ammonium thiocyanate, 16, 74 Ammonium vanadate, 13, 1 to w-Amyl alcohol, IS, 17 hri.-Amyl alcohol, 13, 68 -Amylbenzene, 10, 4 -Amyl borate, 13, 17 -Amyl bromide, 16, 41 iso-Amyl iodide, 13, 62 n-Amyl iodide, 13, 62 n-Amybnagnesium bromide, 16, 41... 

Pyrogels used by the US armed forces include (1) PT1, which is a complex mixt based on a paste of Mg and an oxidizer, bound with petroleum distillate and asphalt. Isobutyl methacrylate is used as a thickener. (2) PT2, which contains 5% isobutyl methacrylate as a thickener, together with Ba nitrate and a small quantity of asphalt. (3) PTV, which is described as an improved oil and metal incendiary mixt composed of 5% poly butadiene, 6% Na nitrate, 28% Mg, and a trace of p-aminophenol in 60% gasoline (Ref 5)... 

Polypyrrole shows catalytic activity for the oxidation of ascorbic acid,221,222 catechols,221 and the quinone-hydroquinone couple 223 Polyaniline is active for the quinone-hydroquinone and Fe3+/Fe2+ couples,224,225 oxidation of hydrazine226 and formic acid,227 and reduction of nitric acid228 Poly(p-phenylene) is active for the oxidation of reduced nicotinamide adenine dinucleotide (NADH), catechol, ascorbic acid, acetaminophen, and p-aminophenol.229 Poly(3-methylthiophene) catalyzes the electrochemistry of a large number of neurotransmitters.230... 

---