2,4,6-Trinitrophenol

Bezeichnung:2,4,6-Trinitrophenol

CAS-Nr88-89-1

Englisch Name:PICRIC ACID

CBNumberCB1195194

SummenformelC6H3N3O7

Molgewicht229.1

MOL-Datei88-89-1.mol

Synonyma

Pikrinsure

2,4,6-Trinitrophenol

2,4,6-Trinitrophenol physikalisch-chemischer Eigenschaften

Schmelzpunkt	122-123 °C (dried material, Lit. Merck Index 12^th Ed.)(lit.)
Siedepunkt	300℃
Dichte	1.00 g/mL at 20 °C
Dampfdichte	7.9 (vs air)
Dampfdruck	1 mm Hg ( 195 °C)
Brechungsindex	1.7630 (estimate)
Flammpunkt	150℃
storage temp.	Store at RT.
Löslichkeit	alcohol: soluble1 (g/12 mL)(lit.)
pka	0.38(at 25℃)
Colour Index	10305
Aggregatzustand	solution (saturated aqueous)
Wichte	1.005
Farbe	yellow solution
Säure-Base-Indikators(pH-Indikatoren)	0.2(colourless)-1(yellow)
Explosionsgrenze	0.01%
Wasserlöslichkeit	(mg/L): 66,670 at 100 °C (quoted, Windholz et al., 1983) 14,000 at 20 °C, 68,000 at 100 °C (quoted, Verschueren, 1983)
maximale Wellenlänge (λmax)	354nm
Merck	13,7492
BRN	423400
Expositionsgrenzwerte	TLV-TWA skin 0.1 mg/m³ (ACGIH, OSHA, and MSHA).
Stabilität	Stability Unstable; may detonate if struck, heated or ground. Highly flammable if dry. May explode if dry - keep wet at all times. Keep water content above 20%. Flammable. Incompatible with strong oxidizing agents, bases, most common metals, ammonia, strong reducing agents. Avoid shock, friction, heat. Compounds formed by reaction with
Major Application	Explosives, power circuits, energetic materials, liquefied gas fuels, thin films, power generation, batteries, fuel cells, steel, gold films, nanopowder, antifreeze fluid for automobiles, polymerization inhibitors, tattoo removal from skin, antiinfiammatroy agent, treatment of neoplasm
InChIKey	OXNIZHLAWKMVMX-UHFFFAOYSA-N
CAS Datenbank	88-89-1(CAS DataBase Reference)
EPA chemische Informationen	Picric acid (88-89-1)

Sicherheit

Kennzeichnung gefährlicher	F,T,E,Xn
R-Sätze:	1-4-11-23/24/25-2-36-20/21/22-3
S-Sätze:	35-45-37-28-36/37-36-26-16-25
RIDADR	UN 1344 4.1/PG 1
OEB	D
OEL	TWA: 0.1 mg/m3, STEL: 0.3 mg/m3 [skin]
WGK Germany	2
RTECS-Nr.	TJ7875000
HazardClass	4.1
PackingGroup	I
Giftige Stoffe Daten	88-89-1(Hazardous Substances Data)
Toxizität	LC50 (48-h) for red killifish 513 mg/L (Yoshioka et al., 1986).
IDLA	75 mg/m3

Gefahreninformationscode (GHS)

PICRIC ACID Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
GELBE KRISTALLE
PHYSIKALISCHE GEFAHREN
Fließen, Schütten o.ä. kann zu elektrostatischer Aufladung führen. Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich.
CHEMISCHE GEFAHREN
Bei Stoß, Reibung oder Erschütterung explosionsartige Zersetzung möglich. Kann beim Erhitzen explodieren. Bildung stoßempfindlicher Verbindungen mit Metallen, insbesondere Kupfer, Blei, Quecksilber und Zink. Beim Verbrennen Bildung von giftigen Kohlen- und Stickoxiden. Reagiert heftig mit Oxidationsmitteln und Rreduktionsmitteln.
ARBEITSPLATZGRENZWERTE
TLV: 0,1 mg/m?als TWA (ACGIH 2008).
MAK: Hautresorption (H); Sensibilisierung der Haut (Sh); Krebserzeugend Kategorie 3B (DFG 2008).
AUFNAHMEWEGE
Aufnahme in den Körper durch Verschlucken.
INHALATIONSGEFAHREN
Verdampfung bei 20°C vernachlässigbar; eine gesundheitsschädliche Partikelkonzentration in der Luft kann jedoch schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt schwachdie Augen
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann Dermatitis hervorrufen. Möglich sind Auswirkungen auf den Magendarmtrakt, die Nieren, die Leber und das Blut nach Verschlucken.
LECKAGE
Zündquellen entfernen. Gefahrenbereich verlassen! Fachmann zu Rate ziehen! Persönliche Schutzausrüstung: Atemschutzgerät mit Partikelfilter entsprechend der Arbeitsplatzkonzentration des Stoffes. Verschüttetes Material in Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. NICHT in die Umwelt gelangen lassen.
R-Sätze Betriebsanweisung:
R1:In trockenem Zustand explosionsgefährlich.
R4:Bildet hochempfindliche explosionsgefährliche Metallverbindungen.
R11:Leichtentzündlich.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R2:Durch Schlag, Reibung, Feuer oder andere Zündquellen explosionsgefährlich.
R36:Reizt die Augen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S35:Abfälle und Behälter müssen in gesicherter Weise beseitigt werden.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S37:Geeignete Schutzhandschuhe tragen.
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S25:Berührung mit den Augen vermeiden.
Aussehen Eigenschaften
2,4,6-Trinitrophenol, C6H3N3O7.
Gefahren für Mensch und Umwelt
Explosionsgefahr beim Erhitzen;
Gefährliche Zersetzungsprodukte: Kohlenmonoxid, nitrose Gase
Gefährliche Reaktionen mit: Alkalihydroxiden, Alkalimetallen, Metallen, Metallsalzen, Fluor.
Im trockenen Zustand explosionsgefährlich; bildet hochempfindliche, explosionsgefährliche Metallverbindungen.
Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
Schleimhautreizungen (Mund, Augen), Dermatitis, nach Verschlucken großer Mengen Magenkrämpfe und Erbrechen. Toxische Wirkung auf Leber und Nieren. LD50 (oral, Kaninchen) 120 mg/kg (wasserfrei).
Biologische effekte: Wasserorganismen LC50 287 mg/l, Arthropoden (daphnia magna) EC50 112 mg/l.
Abbaubarkeit: CSB 0.92, ThSB 0.98 Wassergefährdend (WGK 2).
Schutzmaßnahmen und Verhaltensregeln
Nur für Sachkundige zugänglich aufbewahren.
Bei Auftreten von Stäuben Filter 89 B/St
Schutzbrille mit Seitenschutz und oberer Augenraumabdeckung
Neopren-Schutzhandschuhe als kurzzeitiger Spritz- und Staubschutz.
Verhalten im Gefahrfall
Reinigungsverfahren: Feucht halten, vorsichtig aufnehmen, entsorgen, nachreinigen, bis zur Entsorgung feuchthalten
Wassernebel, Wasserstrahl, Schaum
Erste Hilfe
Nach Hautkontakt: Mit viel Wasser waschen, mit Polyethylenglykol 400 abtupfen.
Nach Augenkontakt: 15 Minuten bei gespreizten Lidern unter fließendem Wasser mit Augendusche ausspülen. Augenarzt konsultieren!
Nach Einatmen: Frischluft, ggf. Atemspende/Gerätebeatmung
Nach Verschlucken: Viel wasser trinken lassen, Erbechen auslösen, Arzt konsultieren.
Nach Kleidungskontakt: Verunreinigte Kleidung sofort ausziehen, ggf. auch die Unterwäsche.
Paraffinöl (3ml/kg), Natriumsulfat (1EL/0,25l), Aktivkohle.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Falls Recycling nicht möglich, als Sonderabfall entsorgen, zuständige Stellen: Hubland-Herr Riepl:8884711, Klinikum-Herr Uhl:2015557.
Beschreibung
Picric acid is a white to yellowish crystalline substance, soluble in most organic solvents and highly flammable. Picric acid is a derivative of phenol. It reacts with metals to form metal picrates, which like picric acid itself are highly sensitive. It is often used for tissue fixative (Bouin solution) for histology specimens, as a booster to detonate another, less sensitive explosive, such as trinitotoluene (TNT). It is used in the manufacture of fireworks, matches, electric batteries, coloured glass, dyes, antiseptics, explosives, disinfectants, leather industries, pharmaceutical, and textile. Picric acid is also used as a yellow dye, as an antiseptic, and in the synthesis of chloropicrin, or nitro-trichloromethane. Picric acids are highly sensitive to heat, shock, or friction and because of the explosive nature it is among the most hazardous substances found in the laboratory.
Chemische Eigenschaften
Picric acid is a highly flammable, white to yellowish crystalline substance. It used in the manufacture of fi reworks, matches, electric batteries, colored glass, explosives, and disinfectants. Pharmaceutical, textile, and leather industries also make use of picric acid.
Chemische Eigenschaften
Also known as picronitric acid, trinitrophenol, nitroxanthic acid, carbazotic acid or phenoltrinitrate, C6H2(N02)3OH is yellow crystals that are soluble in water, alcohol, chloroform, benzene, and ether with a very bitter taste. It is derived by the nitration of phenolsulfonic acid, obtained by heating phenol with concentrated sulfuric acid, and is used for explosives, matches, electric batteries, and etching copper.
Chemische Eigenschaften
Picric acid is a pale yellow, odorless solid. Usually found in solution with 10%20% water. Must be kept wetted; the crystalline form is highly unstable. The dry crystal form is explosive upon rapid heating or mechanical shock.
Physikalische Eigenschaften
White to yellow crystals. Usually present in moist forms because dry picric acid is shock sensitive.
Verwenden
Picric acid and its metal salts are used as explosives. It is also used in making matches; electric batteries, colored glass; in etching copper; and for dyeing textiles.
Verwenden
Preparation of organic derivatives for identification.
Verwenden
Explosives, matches; in leather industry; electric batteries; etching copper; manufacture of colored glass; textile mordant; also as reagent.
Definition
A yellow crystalline solid made by nitrating phenolsulfonic acid. It is used as a dye and as an explosive. With aromatic hydrocarbons picric acid forms characteristic charge-transfer complexes (misleadingly called picrates), used in analysis for identifying the hydrocarbon.
Vorbereitung Methode
Picric acid is used in making explosives; as a burster in projectiles; in rocket fuels, fireworks, colored glass, batteries, and disinfectants; in the pharmaceutical and leather industries; as a fast dye for wool and silk; in metal etching and photographic chemicals; and as a laboratory reagent.
Allgemeine Beschreibung
A paste or slurry consisting of the yellow crystalline solid mixed with water. The dry compound is a sensitive high explosive. The mixture with water is considered safe for storage, handling and shipping. Can be detonated with a number 8 electric blasting cap. The primary hazard is blast where the entire load explodes instantaneously and not from flying projectiles fragments. Can explode under prolonged exposure to heat.
Air & Water Reaktionen
Water soluble.
Reaktivität anzeigen
PICRIC ACID undergoes vigorous reactions with both oxidizing or reducing agents. Burns if ignited by a flame and continues to burns quietly if the quantity is small or, if large, is thinly spread over an area. The dry compound can explode if shocked or exposed to heat. Wetting significantly reduces the tendency to explode. Readily forms salts on contact with many metals (including copper, lead, mercury, zinc, nickel, iron) . The salts are sensitive explosives when subjected to heat, friction, or impact. Contact with concrete floors may form the friction-sensitive explosive calcium picrate [Urbanski, 1964, vol. 1, p. 518]. Contact with metallic zinc or lead can cause detonation. Salts with ammonia, amines and complexes with hydrocarbons are less sensitive [Kirk-Othmer, 1965, vol. 8, p. 617].
Health Hazard
Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution.
Health Hazard
Exposures to picric acid cause different adverse effects on the skin of animals and humans, such as allergies, dermatitis, irritation, and sensitization. Absorption of picric acid by the system causes headache, fever, nausea, diarrhea, and coma. In high concentrations, picric acid is known to cause damage to the erythrocytes, kidneys, and liver.
Health Hazard
Picric acid is a highly toxic substance. Ingestion can cause severe poisoning in humans. The toxic symptoms are headache, nausea, vomiting, abdominal pain, and yellow coloration of the skin. High doses can cause destruction of erythrocytes, gastroenteritis, nephritis, hepatitis, and hematuria. Contact with the eyes can produce irritation and corneal injury. Skin contact with powder can result in sensitization dermatitis. The lethal dose (oral) in rabbits is 120 mg/kg.
Brandgefahr
Picric acid is a high explosive. It is as stable as TNT and about as sensitive to explosive decomposition as TNT. It reacts with many metals and bases, readily forming metal picrates, which are highly sensitive explosive compounds. Metal picrates of iron(III), copper(II), and lead in the dry state are as sensitive as PETN. Its sensitivity is reduced by wetting with water. It explodes when heated above 300°C (572°F).
Kontakt-Allergie
Contact dermatitis occurred primarily in the explosives industry.
Sicherheitsprofil
Poison by ingestion and subcutaneous routes. Mutation data reported. An irritant and an allergen. Shin contact can cause local and systemic allergic reactions. Flammable solid when exposed to heat or flame; can react vigorously with oxidzing materials. Very unstable. A severe explosion hazard when shocked or exposed to heat. It forms salts easily, and many of its salts, known as picrates, are more sensitive explosives than picric acid. It forms unstable salts with concrete, NH3, bases, and metals (e.g., copper, lead, mercury, and zinc). Many of these are heat-, friction-, or impact- sensitive. Mixtures with uranium perchlorate are extremely powerful explosives. mxtures with aluminum and water igmte after a delay period. Can react vigorously with reducing materials. Used in synthesis of dyes, as a drug, to manufacture explosives and matches, to etch copper, and to make colored glass. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS and EXPLOSIVES, HIGH.
mögliche Exposition
Picric acid is used in the synthesis of dye intermediates and in manufacturing picrates; in the manufacture of explosives, rocket fuels; fireworks, colored glass; matches, electric batteries; and disinfectants. It is also used in the pharmaceutical and leather industries; in copper and steel etching; forensic chemistry; histology, textile printing; and photographic emulsions.
Carcinogenicity
Picric acid was mutagenic in the Ames Salmonella assay in the presence of metabolic activation.
Environmental Fate
Chemical/Physical. Picric acid explodes when heated >300 °C (Weast, 1986). Shock sensitive! (quoted, Keith and Walters, 1992).
Versand/Shipping
UN0154 Picric acid, dry or wetted with ＜30% water, by mass, Hazard Class: 1D; Labels:1D-Explosive (with a mass explosion hazard); D-Substances or articles which may mass detonate (with blast and/or fragment hazard) when exposed to fire. UN1344 Picric acid, wetted with not less than 30% water, Hazard Class: 4.1; Labels: 4.1-Flammable solid.
läuterung methode
Crystallise the acid first from acetic acid, then acetone, toluene, CHCl3, aqueous 30% EtOH, 95% EtOH, MeOH or H2O. Dry it in a vacuum for 2hours. Alternatively, dry it over Mg(ClO4)2 or fuse (CARE) and allow it to solidify under a vacuum three times. Because it is EXPLOSIVE, picric acid should be stored moistened with H2O, and only small portions should be dried at any one time. The dry acid should NOT be heated. [Beilstein 6 IV 1388.]
Toxicity evaluation
Metabolic and respiratory acidosis is thought to be the main consequence of picric acid exposure, and is typically the cause of death when reported. An uncoupler of mitochondrial metabolism, picric acid can destroy erythrocytes, cause gastroenteritis, hemorrhagic nephritis, and acute hepatitis. Reduction to the N-acetyl derivative may also play a role in its inherent toxicity.
Inkompatibilitäten
Explosive when dry. Violent reaction with oxidizers and reducing materials. Air or oxygen is not required for decomposition. Shock sensitive compounds can be formed on contact with plaster, concrete. An explosive mixture results when the aqueous solution crystallizes. May explosively decompose from heat, shock, friction, or concussion. Copper, lead, zinc and other metals, or their salts can form other salts that are initiators and much more sensitive to shock than this chemical. Corrodes metals.
Waste disposal
Controlled incineration in a rotary kiln incinerator equipped with particulate abatement and wet scrubber devices.
Vorsichtsmaßnahmen
Workers should use protective clothing, avoid skin contact, and use goggles and face masks to avoid dust.
Einzelnachweise
https://en.wikipedia.org/wiki/Picric_acid
https://pubchem.ncbi.nlm.nih.gov/compound/picric_acid#section=InChI

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