1,4-Dihydroxybenzol

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H302：Gesundheitsschädlich bei Verschlucken.

  H318：Verursacht schwere Augenschäden.

  H341：Kann vermutlich genetische Defekte verursachen.

  H351：Kann vermutlich Krebs verursachen.

  H410：Sehr giftig für Wasserorganismen mit langfristiger Wirkung.

• Sicherheit

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P273：Freisetzung in die Umwelt vermeiden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

Hydroquinone Chemische Eigenschaften,Einsatz,Produktion Methoden

• ERSCHEINUNGSBILD

  FARBLOSE KRISTALLE.

• PHYSIKALISCHE GEFAHREN

  Staubexplosion der pulverisierten oder granulierten Substanz in Gemischen mit Luft möglich.

• CHEMISCHE GEFAHREN

  Reagiert sehr heftig mit Natriumhydroxid.

• ARBEITSPLATZGRENZWERTE

  TLV: 2 mg/m?(als TWA); Krebskategorie A3 (bestätigte krebserzeugende Wirkung beim Tier mit unbekannter Bedeutung für den Menschen); (ACGIH 2005).
  MAK: Hautresorption; Krebserzeugend Kategorie 2; Keimzellmutagen Kategorie 3A; (DFG 2005).
  

• AUFNAHMEWEGE

  Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.

• INHALATIONSGEFAHREN

  Beim Verdampfen bei 20°C tritt eine gesundheitsschädliche Kontamination der Luft nicht oder nur sehr langsam ein

• WIRKUNGEN BEI KURZZEITEXPOSITION

  WIRKUNGEN BEI KURZZEITEXPOSITION:
  Die Substanz reizt stark die Augen. Die Substanz reizt die Haut und die Atemwege.

• WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION

  Wiederholter oder andauernder Hautkontakt kann zu Dermatitis und Hautsensibilisierung führen. Möglich sind Auswirkungen auf Augen und Haut. Führt zu Verfärbung der Bindehaut und Hornhaut, sowie Pigmentverlust der Haut. Möglicherweise krebserzeugend für den Menschen.

• LECKAGE

  Verschüttetes Material in abdichtbaren Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzgerät, P2-Filter für schädliche Partikel. NICHT in die Umwelt gelangen lassen.

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R40:Verdacht auf krebserzeugende Wirkung.
  R41:Gefahr ernster Augenschäden.
  R43:Sensibilisierung durch Hautkontakt möglich.
  R50:Sehr giftig für Wasserorganismen.
  R68:Irreversibler Schaden möglich.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
  S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.

• Aussehen Eigenschaften

  1,4 - Hydrochinon
  Summenformel: C6H6O2

• Gefahren für Mensch und Umwelt

  Gesundheitsschädlich beim Einatmen und Verschlucken.
  Zu vermeidende Bedingungen: Licht- und Luftempfindlich. Zu vermeidende Stoffe: Starke Oxidationsmittel, Säuren. Säureanhydride, Säurechloride, Eisen und Eisensalze.
  Gefährliche Zersetzungsprodukte: Kohlenmonoxid, Kohlendioxid,
  Gesundheitsschädlich beim Verschlucken, Einatmen oder Aufnahme durch die Haut.
  Reizt die Augen und die Haut. Reizwirkung auf die Schleimhäute und die oberen Atemwege. Fruchtschädigende Substanz.
  Krebserzeugend (Gr. III A 2; DFG)
  Wassergefährdungsklasse 2 (Nr. 128)

• Schutzmaßnahmen und Verhaltensregeln

  Behälter dicht geschlossen halten. An einem trockenen, kühlen Platz lagern.
  Schutzbrille mit Seitenschutz.
  Chemikalienresistente Schutzhandschuhe.

• Verhalten im Gefahrfall

  Feste Bestandteile mechanisch aufnehmen. Nicht in Oberflächenwasser und Kanalisation gelangen lassen.
  Geeignete Löschmittel: Kohlendioxid, Trockenlöschmittel oder geeigneter Schaum.

• Erste Hilfe

  Nach Hautkontakt: Nach Berührung sofort mit Seife und viel Wasser abwaschen.
  Nach Augenkontakt: 15 Minuten bei gespreizten Lidern unter fließendem Wasser ausspülen. Augenarzt konsultieren!
  Nach Einatmen: Nach Einatmen, Person sofort an die frische Luft bringen.
  Nach Verschlucken: Reichlich Wasser nachtrinken und unverzüglich Arzt zu Rate ziehen.
  Nach Kleidungskontakt: Benetzte Kleidungsstücke sofort ausziehen, ggf. auch die Unterwäsche.
  Ersthelfer: siehe gesonderten Anschlag

• Sachgerechte Entsorgung

  Falls Recycling nicht möglich, die Substanz zur Sonderabfallverbrennung geben. Auskunft: Hr. Riepl (8884711) od. Hr. Uhl für Klinikum (2015557).

• Beschreibung

  Hydroquinone (HQ) is produced by the oxidation of aniline or phenol, by the reduction of quinone, or from a reaction of acetylene and carbon monoxide. Hydroquinone occurs naturally as a glucose ether, also known as arbutin, in the leaves of many plants and in fruits, as well as one of the agents used in the defense mechanism of the bombardier beetle, family Carabidae.

• Chemische Eigenschaften

  white needle-like crystals or crystalline powder

• Chemische Eigenschaften

  Hydroquinone, a colorless, hexagonal prism, has been reported to be a good antimitotic and tumor-inhibiting agent. It is a reducing agent used in a photographic developer, which polymerizes in the presence of oxidizing agents. In the manufacturing industry it may occur include bacteriostatic agent, drug, fur processing, motor fuel, paint, organic chemicals, plastics, stone coating, and styrene monomers.

• Physikalische Eigenschaften

  Colorless to pale brown, odorless, hexagonal crystals

• Originator

  Quinnone,Dermohr,US,1980

• Verwenden

  K channel agonist, antihypertensive

• Verwenden

  Use as photographic reducer and developer; as reagent in the determination of small quantities of phosphate; as antioxidant. Depigmentor

• Verwenden

  Photographic reducer and developer; antioxidant; stabilizing agent for some polymers; intermediate in the manufacturing of some dyes and pigments; in cosmetic formulations.

• Verwenden

  hydroquinone is a pigment-lightening agent used in bleaching creams. Hydroquinone combines with oxygen very rapidly and becomes brown when exposed to air. Although it occurs naturally, the synthetic version is the one commonly used in cosmetics. Application to the skin may cause allergic reaction and increase skin sun sensitivity. Hydroquinone is potentially carcinogenic and is associated with causing ochronosis, a discoloration of the skin. The u.S. FDA has banned hydroquinone from oTC cosmetic formulations, but allows 4 percent in prescription products. Its use in cosmetics is prohibited in some european countries and in Australia.

• Verwenden

  reducing agent prevents polymerization of resin monomers lightens darkened skin, light sensitive

• Definition

  ChEBI: A benzenediol comprising benzene core carrying two hydroxy substituents para to each other.

• Vorbereitung Methode

  There are three current manufacturing processes for HQ: oxidative cleavage of diisopropylbenzene, oxidation of aniline, and hydroxylation of phenol.
  Diisopropylbenzene is air oxidized to the intermediate diisopropylbenzene bishydroperoxide. This hydroperoxide is purified by extraction and reacted further to form hydroquinone. The purified product is isolated by filtration and packaged. The process can be almost entirely closed, continuous, computer-controlled, and monitored.
  HQcan also be prepared by oxidizing aniline to quinone in the presence of manganese dioxide and sulfuric acid. p-Benzoquinone is then reduced to HQ using iron oxide. The resulting hydroquinone is crystallized and dried. The process occurs in a closed system.
  HQis also manufactured by hydroxylation of phenol using hydrogen peroxide as a hydroxylation agent. The reaction is catalyzed by strong mineral acids or ferrous or cobalt salts.

• Indications

  Hydroquinone interferes with the production of the pigment melanin by epidermal melanocytes through at least two mechanisms: it competitively inhibits tyrosinase, one of the principal enzymes responsible for converting tyrosine to melanin, and it selectively damages melanocytes and melanosomes (the organelles within which melanin is stored).

• Manufacturing Process

  Into a pressure reactor there was charged 100 ml of methanol and 1 g of diruthenium nonacarbonyl. The reactor was closed, cooled in solid carbon dioxide/acetone, and evacuated. Acetylene, to the extent of 1 mol (26 g), was metered into the cold reactor. Carbon monoxide was then pressured into this vessel at 835-980 atmospheres, during a period of 16.5 hours; while the reactor was maintained at 100°C to 150°C. The reactor was then cooled to room temperature and opened.
  The reaction mixture was removed from the vessel and distilled at a pressure of 30-60 mm, and a bath temperature of 30°C to 50°C until the methanol had all been removed. The extremely viscous tarry residue remaining in the still pot was given a very crude distillation, the distillate boiling at 82°C to 132°C/2 mm. In an attempt to purify this distillate by a more careful distillation, 5.3 g of a liquid distilling from 53°C to 150°C/5 mm was collected. At this point, much solid sublimate was noted not only in this distillate but in the condenser of the still. 7 g of the solid sublimate was scraped out of the condenser of the still. Recrystallization of the sublimate from ethyl acetate containing a small amount of petroleum ether gave beautiful crystals melting at 175°C to 177°C (5 g). Infrared analysis confirmed that this compound was hydroquinone (9% conversion).

• Trademarks

  Aida;Ambi- skin tone;Black and white;Creme des 3 fleur d'orient;Eldopaque forte;Eldoquin forte 4% cream;Epocler;Esoterica facial;Esoterica regular;Esoterica sensitive skin;Esoterica sunscreen;Melanex topical sollution;Melpaque hp;Melqui hp;Neostrata aha gel;Neostrata hq;Nuquin hp;Pigmanorm;Porcelana;Sinquin;Solaquin forte sun bleaching;Superfade age spot;Ultraquin plaine.

• Therapeutic Function

  Depigmentor

• Weltgesundheitsorganisation (WHO)

  Hydroquinone was introduced in 1965 as a topical depigmenting agent for hyperpigmentation. At high concentrations hydroquinone is corrosive and in most countries has been restricted to the level of approximately 2% and limited to the period of less than 2 months. Additional consideration for restrictive action is that animal experiments have also demonstrated carcinogenic and mutagenic potential of hydroquinone.

• Synthesis Reference(s)

  Chemistry Letters, 14, p. 731, 1985
  The Journal of Organic Chemistry, 50, p. 1722, 1985
  Tetrahedron Letters, 22, p. 2337, 1981 DOI: 10.1016/S0040-4039(01)82900-2

• Allgemeine Beschreibung

  Light colored crystals or solutions. May irritate the skin, eyes and mucous membranes. Mildly toxic by ingestion or skin absorption.

• Air & Water Reaktionen

  Darkens on exposure to air and light. Miscible in water. Solutions become brown in air due to oxidation. Oxidation is very rapid in the presence of alkali.

• Reaktivität anzeigen

  Hydroquinone is a slight explosion hazard when exposed to heat. Incompatible with strong oxidizing agents. Also incompatible with bases. Hydroquinone reacts with oxygen and sodium hydroxide. Reacts with ferric salts . Hot and/or concentrated NaOH can cause Hydroquinone to decompose exothermically at elevated temperature. (NFPA Pub. 491M, 1975, 385)

• Hazard

  Toxic by ingestion and inhalation, irritant. Questionable carcinogen.

• Health Hazard

  Hydroquinone is very toxic; the probable oral lethal dose for humans is 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 150 lb. person. It is irritating but not corrosive. Fatal human doses have ranged from 5-12 grams, but 300-500 mg have been ingested daily for 3-5 months without ill effects. Death is apparently initiated by respiratory failure or anoxia.

• Health Hazard

  Exposures to hydroquinone in large quantities by accidental oral ingestion produce toxicity and poisoning. The symptoms of poisoning include, but are not limited to, blurred speech, tinnitus, tremors, sense of suffocation, vomiting, muscular twitching, headache, convul- sions, dyspnea and cyanosis from methemoglobinemia, coma, and collapse from respira- tory failure. Occupational workers should be allowed to work with protective clothing and dust masks with full-face or goggles to protect the eyes, and under proper management.

• Brandgefahr

  Dust cloud may explode if ignited in an enclosed area. Hydroquinone can react with oxidizing materials and is rapidly oxidized in the presence of alkaline materials. Oxidizes in air.

• Flammability and Explosibility

  Non flammable

• Kontakt-Allergie

  Hydroquinone is used in photography developers (black and white, X-ray, and microfilms), in plastics, in hair dyes as an antioxidant and hair colorant. Hydroquinone is found in many skin bleaching creams.

• Clinical Use

  Hydroquinone is applied topically to treat disorders characterized by excessive melanin in the epidermis, such as melasma. In the United States, nonprescription skin-lightening products contain hydroquinone at concentrations of 2% or less; higher concentrations are available by prescription.

• Nebenwirkungen

  The incidence of adverse effects with hydroquinone increases in proportion to its concentration. A relatively common side effect is local irritation, which may actually exacerbate the discoloration of the skin being treated. Allergic contact dermatitis occurs less commonly. A rare but more serious complication is exogenous ochronosis, in which a yellow-brown pigment deposited in the dermis results in blue-black pigmentation of the skin that may be permanent.

• mögliche Exposition

  Tumorigen,Mutagen; Reproductive Effector; Human Data; PrimaryImritant. Hydroquinone is a reducing agent and is used as anindustrial chemical, chemical intermediate, pharmaceutical,and veterinary drug; as a photographic developer; and as anantioxidant or stabilizer for certain materials, which polymer-ize in the presence of oxidizing agents. Many of its derivativesare used as bacteriostatic agents, and others, particularly 2,5- bis(ethyleneimino) hydroquinone, have been reported to begood antibiotic and tumor-inhibiting agents.

• Erste Hilfe

  If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek med-ical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from ex posure,begin rescue breathing (using universal precautions, includ-ing resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medi-cal attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

• Carcinogenicity

  No case reports of cancer associated with HQ exposure have been published.

• Source

  Hydroquinone occurs naturally in strawberry tree leaves, pears, blackberries, Chinese alpenrose, bilberries, blackberries, hyacinth flowers, anise, cowberries, and lingonberries (Duke, 1992).

• Environmental Fate

  Biological. In activated sludge, 7.5% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Under methanogenic conditions, inocula from a municipal sewage treatment plant digester degraded hydroquinone to phenol prior to being mineralized to carbon dioxide and methane (Young and Rivera, 1985). In various pure cultures, hydroquinone degraded to the following intermediates: benzoquinone, 2-hydroxy-1,4-benzoquinone, and β-ketoadipic acid. Hydroquinone also degraded in activated sludge but no products were identified (Harbison and Belly, 1982). Heukelekian and Rand (1955) reported a 5-d BOD value of 0.74 g/g which is 39.2% of the ThOD value of 1.89 g/g. In activated sludge inoculum, following a 20-d adaptation period, 90.0% COD removal was achieved. The average rate of biodegradation was 54.2 mg COD/g?h (Pitter, 1976).
  Photolytic. A carbon dioxide yield of 53.7% was achieved when hydroquinone adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985). Chemical/Physical. Ozonolysis products reported are p-quinone and dibasic acids (Verschueren, 1983). Moussavi (1979) studied the autoxidation of hydroquinone in slightly alkaline (pH 7 to 9) aqueous solutions at room temperature. The oxidation of hydroquinone by oxygen followed first-order kinetics that yielded hydrogen peroxide and p-quinone as products. At pH values of 7.0, 8.0, and 9.0, the calculated half-lives of this reaction were 111, 41, and 0.84 h, respectively (Moussavi, 1979).
  Chlorine dioxide reacted with hydroquinone in an aqueous solution forming p-benzoquinone (Wajon et al., 1982). Kanno et al. (1982) studied the aqueous reaction of hydroquinone and other substituted aromatic hydrocarbons (aniline, toluidine, 1- and 2-naphthylamine, phenol, cresol, pyrocatechol, resorcinol, and 1-naphthol) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. As the pH was lowered, the amount of cyanogen chloride formed increased (Kanno et al., 1982).
  At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 160, 90, 51, and 29 mg/g, respectively (Dobbs and Cohen, 1980).

• Lager

  (1) Color Code-- Yellow Stripe (strong reducingagent): Reactivity Hazard; Store separately inan area iso-lated from flammables, combustibles, or other yellow-codedmaterials. (2) Color Code- _Blue: Health Hazard/Poison:Store in a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Hydroquinone must be stored to avoid contact withsodium hydroxide since violent reactions occur. Store intightly closed containers in a cool, well-ventilated areaaway from oxidizing materials. Where possible, automati-cally pump liquid from drums or other storage containers toprocess containers.

• Versand/Shipping

  This compound requires aa shipping label of“POISONOUS/TOXIC MATERIALS.”It falls in HazardClass 6.1 and Packing Group II.

• läuterung methode

  Crystallise quinol from acetone, *benzene, EtOH, EtOH/*benzene, water or acetonitrile (25g in 30mL), preferably under nitrogen. Dry it under vacuum. [Wolfenden et al. J Am Chem Soc 109 463 1987, Beilstein 6 H 836, 6 IV 5712.]

• Toxicity evaluation

  Benzene, phenol, and hydroquinone are metabolized in vivo to benzoquinone and excreted as the mercapturate, N-acetyl-S- (2,5-dihydroxyphenyl)-L-cysteine. Hydroquinone is a reducing cosubstrate for peroxidase enzymes, and the resultant semiquinone and p-benzoquinone may bind to DNA.

• Inkompatibilitäten

  Hydroquinone is a reducing agent. Dustforms an explosive mixture with air. May explode on con-tact with oxygen. Incompatible with strong oxidizers, caus-tics; reacts violently with sodium hydroxide. May beoxidized to quinone at room temperatures in the presence ofmoi sture.

Hydroquinone Upstream-Materialien And Downstream Produkte

1,4-Dihydroxybenzol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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