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tert-Butylhydroperoxid
TBHP · tBuOOH · T-BUTYL HYDROPEROXIDE · 2-Hydroperoxy-2-methylpropane · T-Hydro · tert-Butyl hydrogen peroxide · Trigonox · tert-Butyl hydroperoxide Solution
Identifikatoren & physikalische Daten
| CAS No. | 75-91-2 |
|---|---|
| Summenformel | C4H10O2 |
| Durchschnittliche Molmasse | 90,12 g/mol |
| Monoisotopische Masse | 90,06807956 g/mol |
| SMILES | CC(C)(C)OO |
| InChIKey | CIHOLLKRGTVIJN-UHFFFAOYSA-N |
| PubChem CID | 6410 |
| ChEMBL | CHEMBL348399 |
| ChEBI | CHEBI:64090 |
| EC No. | 200-915-7 |
| DTXSID | DTXSID9024693 |
| Lokaler Name | tert-Butylhydroperoxid |
Chemische & physikalische Eigenschaften
| XLogP | 0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 29,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 35 |
| LogP (Verteilungskoeffizient) | -1.3 (calculated) |
| Dichte | 0.88 at 77 °F (USCG, 1999) - Less dense than waterwill float0.8960 g/cu cm at 20 °CRelative density (water = 1): 0.930.86 @25 °C0.937 g/mL at 20 °C |
| Color/Form | LiquidWater-white liquid |
| Löslichkeit | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)Soluble in waterModerately soluble in waterSlightly soluble in waterSoluble in ethanol, ethyl ether, carbon tetrachloride, chloroformFor more Solubility (Complete) data for tert-Butyl hydroperoxide (7 total), please visit the HSDB record page.Miscible |
| Flammpunkt | 80 °F (NTP, 1992)43 °(may explode on heating)Less than 80 °F (less than 27 °C) /closed cup/43 °C85 °F |
| Siedepunkt | 192 °F at 760 mmHg (decomposes)104 °F at 23 mmHg (NTP, 1992)BP: 89 °C (decomposes)BP: 35 °C at 20 mm HgBP: 40 °C at 23 mm Hg37 °C (15 mmHg) |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes.89 °C |
| Schmelzpunkt | 18 °F (NTP, 1992)-8 °CMP: 6 °C-3 °C-2.8 °C |
| Dampfdichte | 2.07 (NTP, 1992) - Heavier than airwill sink (Relative to Air)2.07 (Air = 1)Relative vapor density (air = 1): 3.1 |
| Geruchsschwelle | Odor Threshold Low: 0.05 [ppm] |
| Dampfdruck | 5.46 [mmHg]5.46 mm Hg at 25 °CVapor pressure, kPa at 20 °C: 3.07 (calculated)3.07 [mm Hg] @20 °C62 mmHg at 45 °C |
| Brechungsindex | Index of refraction = 1.4015 at 20 °C/Dn20/D 1.403 |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | pK1: 12.80 (25°C) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| pH | 4.3 |
| Merck | 14,1570 |
| BRN | 1098280 |
| Henry-Konstante | 4.2×100 mol/(m3Pa) at 25℃, Wang et al. (2017) |
| Stabilität | Stable, but may explode if heated under confinement. Decomposition may be accelerated by traces of metals, molecular sieve or other contaminants. Incompatible with reducing agents, combustible material, acids. |
| InChI | 1S/C4H10O2/c1-4(2,3)6-5/h5H,1-3H3 |
| InChIKey | CIHOLLKRGTVIJN-UHFFFAOYSA-N |
| SMILES | CC(C)(C)OO |
| LogP (Verteilungskoeffizient) | 1.230 (est) |
| CAS Datenbank | 75-91-2(CAS DataBase Reference) |
| NIST chemische Informationen | Tert-butyl hydroperoxide(75-91-2) |
| EPA chemische Informationen | tert-Butyl hydroperoxide (75-91-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 17.3% (234 of 1351) of reports. |
|---|---|
| Regulatorische Informationen | Chemical: Hydroperoxide, 1,1-dimethylethylHydroperoxide, 1,1-dimethylethyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hydroperoxide, 1,1-dimethylethyl are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 10-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13623Hydroperoxide, 1,1-dimethylethyl: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Selected organic hydroperoxides: Human health tier II assessment |
| DOT-Kennzeichnung | Organic Peroxide |
| Brandgefahren | Behavior in Fire: May explode in fire (USCG, 1999)Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:May explode from heat or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames. May burn rapidly with flare-burning effect. Containers may explode when heated. Runoff may create fire or explosion hazard. (ERG, 2024)Excerpt from ERG Guide 146 [Organic Peroxides (Heat, Contamination and Friction Sensitive)]:May explode from heat, shock, friction or contamination. May ignite combustibles (wood, paper, oil, clothing, etc.). May be ignited by heat, sparks or flames. May burn rapidly with flare-burning effect. Containers may explode when heated. Runoff may create fire or explosion hazard. (ERG, 2024)Flammable. Many reactions may cause fire or explosion. Risk of fire and explosion on heating. Above 43 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Very dangerous fire hazard when exposed to heat or flame, or by spontaneous chemical reaction such as with reducing materials. |
| Gesundheitsgefahren | Liquid causes severe burns of skin and eyes. (USCG, 1999)Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:Fire may produce irritating, corrosive and/or toxic gases. Ingestion or contact (skin, eyes) with substance may cause severe injury or burns. Runoff from fire control or dilution water may cause environmental contamination. (ERG, 2024)Excerpt from ERG Guide 146 [Organic Peroxides (Heat, Contamination and Friction Sensitive)]: |
| Gefahrenübersicht | TLV Basis: irritation of eyes and respiratory tractRats exposed by inhalation 6 hours/day for 5 days had histological evidence of respiratory irritation at 91 mg/m3 but not at 20 mg/m3 (approximately 6 ppm)[ACGIH] Corrosive to skin[Quick CPC] A corrosive substance that can cause injury to the skin, eyes and respiratory tract[ICSC] Available as a 70% solutionCauses burnsInhalation of high concentration can cause chemical pneumonitis[MSDSonline] |
| Reaktive Gruppe | Peroxides, OrganicWater and Aqueous Solutions |
| UN-Einstufung | UN Hazard Class: 5.2UN Pack Group: II |
| Special Reports | Preliminary 2D Animation of Events Leading to 2017 Fire at Arkema Chemical Plant in Crosby, Texas.[U.S. Chemical Safety BoardPreliminary 2D Animation of Events Leading to 2017 Fire at Arkema Chemical Plant in Crosby, TexasAvailable from, as of November 27, 2017: http://www.csb.gov/videos/preliminary-2d-animation-of-events-leading-to-2017-fire-at-arkema-chemical-plant-in-crosby-texas/] |
| Reactivity Alerts | ExplosiveStrong Oxidizing Agent |
| Reactivity Profile | Most alkyl monohydroperoxides, such as TERT-BUTYL HYDROPEROXIDE, are liquid. The explosivity of the lower members (e.g., methyl hydroperoxide or possibly traces of the dialkyl peroxides) decreasing with increasing chain length and branching, [Bretherick 2nd ed. 1979 p. 10]. Though relatively stable explosions have been caused by distillation to dryness [Milas, JACS, 1946 68 205] or attempted distillation at atmospheric pressure (Castrantas 1965 p 15). Very soluble in organic solvents and alkali metal hydroxide solutions. Combustible and a moderate fire risk [Hawley].Most alkyl monohydroperoxides are liquid. The explosivity of the lower members (e.g., methyl hydroperoxide, or possibly, traces of the dialkyl peroxides) decreasing with increasing chain length and branching [Bretherick 2nd ed. 1979 p. 10]. Though relatively stable, explosions have been caused by distillation to dryness [Milas, JACS 1946, 68, 205] or attempted distillation at atmospheric pressure [Castrantas 1965 p. 15].Most alkyl monohydroperoxides are liquid, the explosivity of the lower members (e.g., methyl hydroperoxide, or possibly due to traces of the dialkyl peroxides) decreasing with increasing chain length and branching [Bretherick 2nd ed. 1979 p. 10]. Though relatively stable, explosions have been caused by distillation to dryness [Milas, JACS, 1946, 68, 205] or attempted distillation at atmospheric pressure [Castrantas 1965 p 15]. |
| Brandbekämpfung | Fire Extinguishing Agents: Dry chemical, foam or carbon dioxide. (USCG, 1999)Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:SMALL FIRE: Water spray or fog is preferredif water not available use dry chemical, CO2 or regular foam.LARGE FIRE: Flood fire area with water from a distance. Use water spray or fogavoid aiming straight or solid streams directly onto the product. Do not move cargo or vehicle if cargo has been exposed to heat. If it can be done safely, move undamaged containers away from the area around the fire.FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzlesif this is impossible, withdraw from area and let fire burn. (ERG, 2024)Excerpt from ERG Guide 146 [Organic Peroxides (Heat, Contamination and Friction Sensitive)]:Use water spray, dry sand, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Refer for medical attention . |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting. Thus, the risk of increasing the medical problems by inducing vomiting of a volatile corrosive chemical is very high. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:Refer to the "General First Aid" section. Specific First Aid: Contaminated clothing may be a fire risk when dry. (ERG, 2024)Excerpt from ERG Guide 146 [Organic Peroxides (Heat, Contamination and Friction Sensitive)]: |
| Sichere Lagerung | Fireproof. Separated from combustible substances and reducing agents. Cool. Inspect container frequently to identify bulging and leaking. |
| Firefighting Hazards | Hazardous decomposition products formed under fire conditions. - Carbon oxides |
| Brandbekämpfungsverfahren | To fight fire, use alcohol foam, CO2, dry chemical.In case of fire, water should be applied by the sprinkler system or by hose from a safe distance, preferably with a fog nozzle. Foam may be necessary instead if the peroxide is diluted in a low density flammable solvent. Portable extinguishers should not be used except for very small fires. Peroxides threatened by fire should be wetted from a safe distance for cooling. /Peroxides, Organic and Inorganic/Water may be ineffective. Alcohol foam.Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Use water spray to cool unopened containers. |
| Lagerbedingungen | Store in original container. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature 2 - 8 °C |
| Reinigungsverfahren | Spills should be cleaned up promptly using non-sparking tools and an inert, moist diluent such as vermiculite or sand. Sweepings may be placed in open containers or polyethylene bags and the area washed with water and detergent. Spilled, contaminated, waste or questionable peroxides should be destroyed. /Peroxides, Organic and Inorganic/Most peroxides can be hydrolyzed by adding them slowly with stirring to about ten times their weight of cold 10% sodium hydroxide solution. The reaction may require several hours. /Peroxides, Organic and Inorganic/ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations |
| Freisetung ohne Brand | Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Keep combustibles (wood, paper, oil, etc.) away from spilled material. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Keep substance wet using water spray. Stop leak if you can do it without risk.SMALL SPILL: Pick up with inert, damp, non-combustible material using clean, non-sparking tools and place into loosely covered plastic containers for later disposal.LARGE SPILL: Wet down with water and dike for later disposal. Prevent entry into waterways, sewers, basements or confined areas. DO NOT CLEAN-UP OR DISPOSE OF, EXCEPT UNDER SUPERVISION OF A SPECIALIST. (ERG, 2024)Excerpt from ERG Guide 146 [Organic Peroxides (Heat, Contamination and Friction Sensitive)]: |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT absorb in saw-dust or other combustible absorbents. |
| Preventive Measures | Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.Keep away from heat and sources of ignition.ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Wechselwirkungen | In hemoglobin-free perfused rat liver, tert-butylhydroperoxide (0.56 mmol) reversibly decreased metabolism of sodium hexobarbital (0.19 mmol).The current studies have investigated the effect of heterocyclic drugs with the single thiol group (thiamazole, mercaptopurine) and dithiol aliphatic drugs (dimercaptosuccinic acid, dithiothreitol) under oxidative stress conditions, using tert-butyl hydroperoxide (t-BuOOH), in human erythrocyte lysate with the luminol-enhanced chemiluminescence technique. Knowing that oxidative processes induced by t-BuOOH are triggered by (oxy)hemoglobin (Hb), the effect of different thiol drugs (RSH) on isolated human Hb oxidation to methemoglobin (MHb) and hemichromes (HChr) was further considered. Three types of chemiluminescence curves, fitting to logistic-exponential model, have been revealed under influence of RSH. Structure of the data (MHb and HChr production, and free radical activity of RSH) in Principal Component Analysis visualization and kinetic profiles of chemiluminescence integrate information in terms of the diversity of RSH reaction mechanisms depending on the specific molecular context of the given thiol: aliphatic or aromatic nature as well as the number and position of the -SH groups in the molecule. The study conducted in presented in vitro systems indicates the potential role of thiol drugs mediated toxicity in an oxidative stress dependent mechanism.The aim of this study was to investigate the protective effects of 6-shogaol on tert-butyl hydroperoxide (tBHP)-induced oxidative stress leading to apoptosis in human hepatoma cell line HepG2. The cells were exposed to tBHP (100 umol/L) after pretreatment with 6-shogaol (2.5 and 5 umol/L), and then cell viability was measured. 6-Shogaol fully prevented HepG2 cell death caused by tBHP. Treatment of tBHP resulted in apoptotic cell death as assessed by TUNEL assay and the expression of apoptosis regulator proteins, Bcl-2 family, caspases and cytochrome c. Cells treated with 6-shogaol showed rapid reduction of apoptosis by restoring these markers of apoptotic cells. In addition, 6-shogaol significantly recovered disruption of mitochondrial membrane potential as a start sign of hepatic apoptosis induced by oxidative stress. In line with this observation, antioxidative 6-shogaol inhibited generation of reactive oxygen species and depletion of reduced glutathione in tBHP-stimulated HepG2 cells. Taken together, these results for the first time showed antioxidative and antiapoptotic activities of 6-shogaol in tBHP-treated hepatoma HepG2 cells, suggesting that 6-shogaol could be beneficial in hepatic disorders caused by oxidative stress.A nanocarrier, namely, hydroxylethyl-chitosan nanoparticles was developed in this research for delivering antioxidants with 6-hydroxy-2, 5, 7, 8-tetra-methylchromane-2-carboxylic acid (trolox) as a model antioxidant. The trolox-encapsulated chitosan nanoparticles (trolox-CS NPs) were prepared by modifying chitosan with epoxyethane, which self-assembled into NPs and entrapped trolox, and then characterized by their size, size distribution, morphology and in vitro trolox release profile. Intracellular trafficking of CS NPs was observed. The anti-oxidant effect and potential mechanism of trolox-CS NPs were subsequently investigated in RAW264.7 cells. The effects of trolox-CS NPs on RAW264.7 cells damaged by tert-butylhydroperoxide (t-BHP) were determined by MTT assay for cell viability, MDA assay for membrane lipid peroxidation, JC-1 probe and Annexin V-FITC/PI double staining for mitochondria membrane potential (MMP) and RAW264.7 apoptosis, respectively. The trolox-CS NPs significantly improved cell viability and reduced MDA content compared with those of cells treated with free trolox. The trolox-CS NPs treatment inhibited MMP collapse and RAW264.7 apoptosis more obviously than free trolox. Molecular basis of apoptosis studied by western blotting revealed that trolox-CS NPs may block mitochondria-mediated apoptosis pathway through up-regulation of Bcl-2 and down-regulation of Bax and inhibiting the activation of pro-caspase 3, PARP and Bid.For more Interactions (Complete) data for tert-Butyl hydroperoxide (22 total), please visit the HSDB record page. |
| Ökotoxizitätswerte | LC50Species: Pimephales promelas (Fathead minnow)Conditions: semi-static (daily renewal), 24.4-24.9 °C, pH 7.7-7.9, hardness 210 mg/LConcentration: 29 mg/L for 96 hr /from table/Species: Poecilia reticulata (Guppy)Conditions: semi-static (renewal at 48 hr), 22-24 °C, pH 7.9-8.3, hardness 210 mg/LConcentration: 57 mg/L for 96 hr /from table/EC50Species: Daphnia magna (Water flea)Conditions: static, 20.6-20.8 °C, pH 7.4-7.9, hardness 210 mg/LConcentration: 14 mg/L for 48 hrEffect: immobility /from table/Species: Selenastrum capricornutum (algae)Conditions: static, 23 °C, pH 7.9-8.6, hardness 24 mg/LConcentration: 1.5 mg/L for 72 hrEffect: exponential growth rate /from table/For more Ecotoxicity Values (Complete) data for tert-Butyl hydroperoxide (6 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 86(SRC), determined from a structure estimation method(2), indicates that tert-butyl hydroperoxide is expected to have high mobility in soil(SRC). However, hydroperoxides react with a variety of compounds and are reduced readily to the corresponding alcohols(3). They are decomposed readily by multivalent metal ions, are photo- and thermally sensitive and undergo initial oxygen-oxygen bond homolysis, and they are attacked readily by free radicals, undergoing induced and self-induced decomposition(3). Chemical degradation is expected to be the dominant fate process in soil(SRC). The pKa of tert-butyl hydroperoxide is 12.80(4), indicating that this compound will exist in the unionized form in the environment. Volatilization of tert-butyl hydroperoxide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(2). tert-Butyl hydroperoxide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.46 mm Hg at 25 °C(5). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 86(SRC), determined from a structure estimation method(2), indicates that tert-butyl hydroperoxide is not expected to adsorb to suspended solids and sediment(SRC). However, hydroperoxides react with a variety of compounds and are reduced readily to the corresponding alcohols(3). They are decomposed readily by multivalent metal ions, are photo- and thermally sensitive and undergo initial oxygen-oxygen bond homolysis, and they are attackec readily by free radicals, undergoing induced and self-induced decompositions(3). Chemical degradation is expected to be the dominant fate process in water(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.6X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 20 days, respectively(SRC). A pKa of 12.8(5) indicates tert-butyl hydroperoxide will exist in the unionized form at pH values of 5 to 9(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 0.94(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 0% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in atmosphere(1), tert-butyl hydroperoxide, which has a vapor pressure of 5.46 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tert-butyl hydroperoxide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 4 days(SRC), calculated from its rate constant of 3.0X10-12 cu cm/molecule-sec at 25 °C(3). tert-Butyl hydroperoxide will directly photolyze with breakage of the peroxide bond(4). |
| Unerwünschte Wirkungen | Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.ACGIH Carcinogen - Suspected Human. |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: tert-Butyl Hydroperoxide is a water-white liquid. It is used to introduce peroxy group into organic molecules, as a reagent in radical substitution reactions, and catalyst in polymerization reactions. HUMAN STUDIES: The main toxic effect of most peroxides is irritation of skin, mucous membranes and eyes. Prolonged or intense skin contact or splashes in the eyes may cause severe injury. Some organic peroxide vapors are irritating and may also cause headaches, intoxication similar to alcohol, and lung edema if inhaled in high concentrations. Some are skin sensitizers. Hydroperoxides are extremely irritating and corrosive to the eyes, with risk of blindness, and may cause serious injury or death if ingested in sufficient quantity. tert-Butyl hydroperoxide induced DNA lesions in human liver cells, and stimulated activity of superoxide dismutase and mainly glutathione peroxidase. A slight increase in the gene expression of Cu/Zn superoxide dismutase and catalase with 500 uM tert-butyl hydroperoxide and of catalase with 200 uM hydrogen peroxide was observed in HepG2 cells in culture. tert-Butyl hydroperoxide has been demonstrated to induce apoptosis in hepatoma cell line HepG2. ANIMAL STUDIES: When tested as a 75% solution in dimethylphthalate by application of two drops to rabbit eyes, it caused injury graded 5 on a scale of 0 to 7. A drop of 35% solution in propylene glycol caused a reaction graded between 46 and 79 on a scale of 0 to 100, persisting at least a week. A 7% solution in the same solvent was the maximum which could be tolerated without significant irritation. In a routine primary skin irritation assay, three out of six rabbits died. The peroxide is a severe dermal irritant. It can also be absorbed through the skin in toxic amounts to cause cyanosis, depression, loss of righting, blanching of the treated skin, convulsions, and death. In male rats serum hepatotoxicity parameters were increased from 2 hr following 1 mmol/kg tert-butyl h |
| Ökotoxizitätsauszüge | /PLANTS/ The effects of TBHP on cell growth (wet weight) and cell membrane integrity (ion leakage) were studied in in vitro tests in which cells of tobacco (Nicotiana tabacum) were exposed in a growth solution. The cells were cultured in a medium (LS-medium) containing macro- and micro-elements. For the determination of cell growth, cells were exposed for 7 days in the LS-medium (test concentrations: 0-9-18-45-90-180 mg/L) after which the fresh weight of the cells was determined. For the determination of cell membrane integrity (determined by measuring continuously the conductivity of the medium that was pumped through a flow conductivity cell during a period of 12 hours), cells from the late exponential growth phase (usually 7-day old cultures) were collected, washed 3 times with "electrical conductivity medium" (EC medium, being a 1/100 dilution of the LS-medium), transferred to EC medium and exposed for 12 hours in this medium (test concentrations: 0-18-45-90-135-180 mg/L). Exposure to TBHP resulted in concentrations-related effects on both cell growth (decrease of fresh weight) and cell membrane integrity (increase of conductivity in the medium), with in both cases a LOEC of 45 mg/L (around 70% reduction of cell culture growth and around 50% increase in conductivitypercentages derived from graphs) and a NOEC of 18 mg/L. Maximum conductivity values after treatment with high concentrations of TBHP did not further increase after freeze-thaw treatment of the cultures and were in the same range as those measured after freeze-thawing of untreated cultures. Hence, according to the authors of this study, the observed increase in conductivity during TBHP treatment was due mainly to an efflux of ions caused by membrane damage rather than to a metabolic response of the cells to TBHP or to generation of ions by the reaction of TBHP with cellular components. In earlier in vitro tests with terrestrial plant tissues, viz. (discs) of egg plant fruit, white gourd, chayote frui |
| Signs and Symptoms | Burning sensation. Cough. Laboured breathing.Pain. Redness. Blisters.Redness. Pain. Severe deep burns.Abdominal cramps. Burning sensation. Weakness. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for tert-butyl hydroperoxide is available.[Available from, as of November 3, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status] |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of tert-butyl hydroperoxide can be estimated to be 86(SRC). According to a classification scheme(2), this estimated Koc value suggests that tert-butyl hydroperoxide is expected to have high mobility in soil. However, hydroperoxides react with multivalent metal ions and other species ubiquitous in soil and are readily reduced to the corresponding alcohols(3). Therefore, it is expected to chemically degrade rapidly in soil and is not expected to travel long distances in soil or migrate to groundwater(SRC). The pKa of tert-butyl hydroperoxide is 12.8(4), indicating that this compound will exist in the un-ionized form in the environment. |
| TSCA Test Submissions | The ability of t-butyl hydroperoxide to induce morphological transformation in the C3H/10T1/2 mouse cell line (Cell Transformation Assay) was evaluated at concentrations of 4.9, 2.4, 1.2, 0.6 and 0.3 nl/ml in acetone, with corresponding survival ranging from 86.3% to 44.7%. None of the tested concentrations produced significantly greater transformation frequencies relative to the solvent control.The mutagenicity of t-butyl hydroperoxide was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537, and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat or hamster liver S9 fraction. Based on preliminary bacterial toxicity determinations, aqueous t-butyl hydroperoxide was tested for mutagenicity at concentrations of 3.0, 15, 75, 150, and 300 ug/plate using a 20-minute preincubation technique. t-Butyl hydroperoxide caused a reproducible positive response in tester strains TA98, TA100 and TA1537 in tests with added metabolic activation.The ability of aqueous t-butyl hydroperoxide to induce specific locus mutations at the TK locus in cultured L5178Y mouse lymphoma cells (Mouse Lymphoma Mutagenesis Assay) was evaluated in the presence and absence of Aroclor-induced rat liver S9 metabolic activation. Based on preliminary toxicity tests, nonactivated cultures were treated with 1.3, 1.8, 2.4, 3.2, 4.2, 5.6, 7.5, 10, and 13 nl/ml, and S9-activated cultures were treated with 13, 18, 24, 32, 42, 56, 75, 100, 130, and 180 nl/ml. Cloning efficiency ranged from 3-92% for nonactivated cultures and from 4-105% for S9-activated cultures. Nonactivated and activated cultures produced mutant frequencies ranging from 2-10.6 and 2-8 times that of the solvent controls (water), respectively, with a clear dose-response relationship obtained.The ability of tert-butyl hydroperoxide to cause chromosome aberration was evaluated in bone marrow cells of Sprague-Dawley rats (10/sex/groupexcept for high dose animals 15/sex) receiving nominal concentrations of test material at 0, 10 30, 75 and 100 ppm in a dynamic air flow chamber for 6 hours/day, for up to five days. There was no effect of treatment as indicated by mortality and gross necropsy observations. Decreased body weights for high dose males (75 & 100 ppm) and high dose females (100 ppm) were observed. None of the treatments produced chromosomal aberrations or damage in bone marrow cells of rats. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Inhalation - burning sensation, cough, labored breathingSkin - redness, pain, blistersEyes - Redness, pain, severe deep burnsIngestion - abdominal cramps, burning sensation, weakness. /From table//SIGNS AND SYMPTOMS/ The main toxic effect of most peroxides is irritation of skin, mucous membranes and eyes. Prolonged or intense skin contact or splashes in the eyes may cause severe injury. Some organic peroxide vapors are irritating and may also cause headaches, intoxication similar to alcohol, and lung edema in inhaled in high concentrations. Some are ... skin sensitizers. Dialkyl peroxides are generally not as strongly irritating, and the diacyl peroxides are the least irritating of the peroxides. Hydroperoxides, peroxyacids and particularly methyl ethyl ketone peroxide are much more severe. They are extremely irritating and corrosive to the eyes, with risk of blindness, and may cause serious injury or death if ingested in sufficient quantity. /Peroxides, Organic and Inorganic//GENOTOXICITY/ This paper presents comparisons of biological impacts of the oxidants H2O2 and t-BHP on human liver cells, and shows modulation of these effects by the phenolic compound carvacrol. To understand better how these oxidants exert their effect on DNA and on the activity of the enzymes superoxide dismutase (SOD) and glutathione peroxidase (GPx), we measured intracellular antioxidant glutathione (iGSH) and intracellular reactive oxidative species (iROS). DNA lesions corresponded to single-strand DNA breaks, alkali-labile lesions and formamido-pyrimidine-DNA-glycosylase (FPG)-sensitive sites. Pre-treatment of cells with carvacrol substantially decreased the number of H2O2-induced DNA lesions, but the number of t-BHP-induced DNA lesions was not reduced. Activities of both SOD and GPx were stimulated significantly by carvacrol and were reduced by the combined effect of carvacrol and oxidants. H2O2 and t-BHP alone influenced the level of antioxidant enzymes differently. While H2O2 did not markedly change the activity of SOD or GPx, lower concentrations of t-BHP stimulated activity of SOD and mainly GPx. The level of iROS was increased by both oxidants and decreased by carvacrol applied either alone or with oxidants. The level of iGSH was not influenced in any of the treatments tested. Our results show that although both oxidants induced oxidative stress and damaged cellular DNA, their influences on other molecular processes were different. The protective effect of carvacrol against DNA-damaging effects of H2O2 was unambiguous, but reduction by carvacrol of the DNA-damaging effect of t-BHP was not observed. These results suggest that the phenolic compound carvacrol contributes to the defense mechanisms of the human organism, but these beneficial effects are dependent on the origin and source of the actual oxidative stress./ALTERNATIVE and IN VITRO TESTS/ Increased oxidative stress is implicated in the onset and progression of prevalent pregnancy disorders (e.g. gestational diabetes and fetal growth restriction), and in programming the fetus to develop metabolic diseases later in life. Since the molecular mechanisms underlying these effects of oxidative stress are largely unexplored, we aimed to investigate if the placental transport of glucose - the main energetic substrate for the fetus and placenta - is altered by oxidative stress. In a human syncytiotrophoblast (STB)cell model, the BeWo cell line,oxidative stress was induced by treatment with 100 mM tert-butylhydroperoxide(tert-BOOH) for 24 hr. Tert-BOOH decreased the steady-state intracellular accumulation (Amax) of[(3)H]2-deoxyglucose([(3)H]DG) mediated by both facilitative(GLUT) and non-facilitative(non-GLUT)glucose transporters. These effects were not associated with a change in the mRNA expression level of GLUT1, the major placental glucose transporter. Also,they seemed to be independent from phosphoinositide 3-kinase and protein kinase C signaling pathways and were unchanged either by inhibitors of free radical-generating enzymes or by free radical scavengers. In contrast, the dietary polyphenols quercetin, epigallocatechin-3-gallate and resveratrol completely reversed the inhibitory effect of tert-BOOH upon[(3)H]DG accumulation through a specific effect on GLUT-mediated transport. Finally, tert-BOOH induced an increase in the transepithelial permeability to [(3)H]DG in the apical-to-basal direction, apparently related to an increase in its paracellular transport. In conclusion, tert-BOOH-induced oxidative stress reduces STB accumulation of glucose associated with an increase in its transepithelial permeability. This effect may contribute to the deleterious consequences of pregnancy disorders associated with oxidative stress.For more Human Toxicity Excerpts (Complete) data for tert-Butyl hydroperoxide (10 total), please visit the HSDB record page. |
| F | 3-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3109 5.2 |
| Zollcode | 29094990 |
| RTECS-Nr. | EQ4900000 |
| R-Sätze (R) | 7-10-20/21/22-34-65-52/53-43-67-53-68-51/53-23-21/22 |
| Toxizität | LD50 oral (rat) 406 mg/kg LD50 skin (rabbit) 460 mg/kg LC50 inhal (rat) 500 ppm (4 h) |
| Gefahrensymbole | O,C,N,T |
| Sicherheitshinweise (S) | 14-3/7-61-45-36/37/39-24-17-16-14A-26-62-47-43 |
| Gefahrenklasse | 5.2Acute Tox. 2 InhalationAcute Tox. 3 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Flam. Liq. 3Muta. 2Org. Perox. FSkin Corr. 1CSkin Sens. 1STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 5.2 - Organic peroxides and self-reacting hazardous materials |
| Gefahrstoffdaten | 75-91-2(Hazardous Substances Data) |
| Selbstentzündungstemperatur | Self-accelerating decomposition at 88 to 93 °C |
Anwendungen & Verwendung
Verwenden
tert-Butyl hydroperoxide is used as an initiator for radical polymerization and in various oxidation process such as sharpless epoxidation. It is involved in osmium catalyzed vicinal hydroxylation of olefins under alkaline conditions. Furthermore, it is used in catalytic asymmetric oxidation of sulfides to sulfoxides using binaphthol as a chiral auxiliary and in the oxidation of dibenzothiophenes. It plays an important role for the introduction of peroxy groups in organic synthesis.
Beschreibung
Tert-butyl hydroperoxide is an alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes. It has a role as an antibacterial agent and an oxidising agent.