Synthesis of picric acid (2,4,6-trinitrophenol)

Preparation of picric acid

Alternative Names: 2,4,6-Trinitrophenol; Trinitrophenol; Melinite; Carbazotic acid; Picronitric acid;

Preparation of picric acid

Preparation of picric acid

25 g of phenol and 25 g of concentrated sulfuric acid (d=1.84g/ml) in a round-bottom flask equipped with an air condenser are heated together for 6 hours in an oil bath at 120°C. After the material has cooled, it is diluted with 75 g of 72% sulfuric acid (d=1.64g/ml). To the resulting solution, in an Erlenmeyer flask, 175 ml of 70% nitric acid (d=1.42 g/ml) is added slowly, a drop at a time, from a drop­ping funnel. When all the nitric acid has been added and the vigorous reaction has subsided, the mixture is heated for 2 hours on the steam bath to complete the nitration. The next morning the picric acid will be found to have separated in crystals. These are transferred to a porcelain filter, washed with small portions of water until the washings are free from sulfate, and dried in the air. The crude product is purified by boiling it with water, in the proportion of 15 g to the liter, filtering hot, and allowing to cool slowly. The heavy droplets of brown oil which dissolve only slowly during this boiling ought to be discarded. Pure picric acid crystallizes from water in pale yellow flat needles, m.p. 122.5° C. It may be obtained in crystals which are almost white by recrystallizing from aqueous hydrochloric acid.

Chemistry of Powder and Explosives, by T. L. Davis, 160-161, 1941

Preparation of picric acid by catalytic process

Preparation of picric acid by catalytic process

Preparation of picric acid by catalytic process

200 g of benzene in a 2-liter round-bottom flask equipped with a condenser is refluxed on the sand bath for 7 hours with 600 ml of nitric acid (d=1.42 g/ml) in which 10 g of mercury(II) nitrate has been dissolved. The material is then transferred to another flask and distilled with steam. Benzene comes over, then nitrobenzene, then finally and slowly a mixture of dinitrobenzene and dinitrophenol. The distillation is con­tinued until all volatile matter has been removed. The liquid in the flask is filtered hot and allowed to crystallize. If the picric acid is not sufficiently pure, it is recrystallized from hot water.

Chemistry of Powder and Explosives, by T. L. Davis, 162, 1941

IUPAC Name

2,4,6-trinitrophenol

InChI

InChI=1S/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H

InChI Key

OXNIZHLAWKMVMX-UHFFFAOYSA-N

Canonical SMILES

C1=C(C=C(C(=C1[N+](=O)[O-])O)[N+](=O)[O-])[N+](=O)[O-]

MeSH Synonyms

2,4,6-trinitrophenol, picrate, picric acid, picric acid, ammonium salt, picric acid, lead (2+) salt, picric acid, potassium salt, picric acid, sodium salt, trinitrophenol

Depositor-Supplied Synonyms

PICRIC ACID, 2,4,6-Trinitrophenol, Trinitrophenol, Melinite, Carbazotic acid, Picronitric acid, Phenol trinitrate, Picral, Acide picrique, Nitroxanthic acid, Phenol, 2,4,6-trinitro-, 88-89-1, Pikrinezuur, Pikrinsaeure, Pikrynowy kwas, Acido picrico, 2-Hydroxy-1,3,5-trinitrobenzene, 1,3,5-Trinitrophenol, 2,4,6-Trinitrophenyl, Phenoltrinitrate, Kyselina pikrova, Acidum picrinicum, C.I. 10305, Pikrinezuur [Dutch], Pikrinsaeure [German], 2,4,6-Trinitrofenol, 2,4,6-Trinitrofenolo, Acide picrique [French], Acido picrico [Italian], Pikrynowy kwas [Polish], Kyselina pikrova [Czech], NSC 36947, picric, UNII-A49OS0F91S, CI 10305, CCRIS 3106, 2,4,6-Trinitrofenol [Dutch], CHEBI:46149, HSDB 2040, Picric acid, dry, Picric acid, wet, 2,4,6-Trinitrofenolo [Italian], OXNIZHLAWKMVMX-UHFFFAOYSA-N, 2,6-Trinitrofenol, EINECS 201-865-9, Pertite, Picric acid (dry), Picric acid (wet), Picric acid solution, 1,5-Trinitrophenol, 2,6-Trinitrofenolo, 2,6-Trinitrophenol, NA1344, UN0154, UN1344, Phenol,4,6-trinitro-, AI3-15403, WLN: WNR BQ CNW ENW, 2-Hydroxy-1,5-trinitrobenzene, Picric acid, dry or wetted with < 30% water, by mass, Trinitrophenol, dry or wetted with < 30% water, by mass, Reflorit, Picricum acidum, Hager’s reagent, PICRICACID, Trinitrophenol [NF], Lyddite (Salt/Mix), Ecrasite (Salt/Mix), Schimose (Salt/Mix), AC1L1NO7, SCHEMBL8745, 2,4,6-trinitro-1-phenol, NA 1344 (Salt/Mix), UN 1344 (Salt/Mix), P6744_SIGMA, 197378_ALDRICH, 239801_ALDRICH, 36011_RIEDEL, 46209_RIEDEL, A49OS0F91S, CHEMBL108541, 131-74-8 (ammonium salt), SCHEMBL14419782, 46209_FLUKA, 573-83-1 (potassium salt), 80450_FLUKA, CTK3E8533, MolPort-001-783-850, 36011_SIAL, LTBB002657, 197378_SIAL, 319287_SIAL, NSC36947, NSC56147, 3324-58-1 (hydrochloride salt), NSC-36947, NSC-56147, AKOS008966816, AN-5561, DB03651, LS-1888, MCULE-8917344355, RTR-027961, UN 0154, 6477-64-1 (lead(2+) salt), Picric acid, wet, with not <10% water, AB1002452, DB-057108, TR-027961, FT-0609916, H2982, 1769-EP2269978A2, 1769-EP2269985A2, 1769-EP2269990A1, 1769-EP2269991A2, 1769-EP2272832A1, 1769-EP2277865A1, 1769-EP2277876A1, 1769-EP2280006A1, 1769-EP2280010A2, 1769-EP2281813A1, 1769-EP2281815A1, 1769-EP2284150A2, 1769-EP2284151A2, 1769-EP2284152A2, 1769-EP2284153A2, 1769-EP2284155A2, 1769-EP2284156A2, 1769-EP2284164A2, 1769-EP2287140A2, 1769-EP2287148A2, 1769-EP2287150A2, 1769-EP2289886A1, 1769-EP2289894A2, 1769-EP2292590A2, 1769-EP2292614A1, 1769-EP2295412A1, 1769-EP2295413A1, 1769-EP2295419A2, 1769-EP2295423A1, 1769-EP2298731A1, 1769-EP2298742A1, 1769-EP2298743A1, 1769-EP2301534A1, 1769-EP2301912A2, 1769-EP2301916A2, 1769-EP2301922A1, 1769-EP2301933A1, 1769-EP2305637A2, 1769-EP2305640A2, 1769-EP2305648A1, 1769-EP2305695A2, 1769-EP2305696A2, 1769-EP2305697A2, 1769-EP2305698A2, 1769-EP2308833A2, 1769-EP2308861A1, 1769-EP2308875A1, 1769-EP2311451A1, 1769-EP2311796A1, 1769-EP2311797A1, 1769-EP2311798A1, 1769-EP2311799A1, 1769-EP2311808A1, 1769-EP2311827A1, 1769-EP2311829A1, 1769-EP2311837A1, 1769-EP2314575A1, 1769-EP2316450A1, 1769-EP2316459A1, 1769-EP2316834A1, 1769-EP2316836A1, 1769-EP2374454A1, 42218-EP2298742A1, 42218-EP2298766A1, 42218-EP2298770A1, 42218-EP2311808A1, 42218-EP2311829A1, 50414-EP2295421A1, 50414-EP2311809A1, 50414-EP2371810A1, 50414-EP2371812A1, A842990, I01-8838, Trinitrophenol, wetted with not <30% water, by mass, Picric acid, wet, with not <10% water [NA1344] [Flammable solid], Picric acid, wet, with not <10% water [NA1344] [Flammable solid], Trinitrophenol or picric acid, dry or wetted with <30% water, by mass, Trinitrophenol, wetted with not <30% water, by mass [UN1344] [Flammable solid], Trinitrophenol, wetted with not <30% water, by mass [UN1344] [Flammable solid], 189195-39-9, 190402-10-9, 29663-11-4, 856615-63-9, 856993-13-0, 857370-42-4, InChI=1/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10, Trinitrophenol or picric acid, dry or wetted with <30% water, by mass [UN0154] [Explosive 1.1D], Trinitrophenol or picric acid, dry or wetted with <30% water, by mass [UN0154] [Explosive 1.1D]

Removed Synonyms

CID6954, TNF, TNP

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3 comments

  1. Kim6964

    This reaction doesn’t work. Since you use the dilute Sulfuric acid(72%) for nitration, It cannot take water molecule so it leads experiment failure.

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