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Dilauroylperoxid
LPO · LAUROYL PEROXIDE · DILAUROYL PEROXIDE · lauroyl · LAURYL PEROXIDE · Dodecanoic peroxyanhydride · laurox · dodecanoyl
Identifikatoren & physikalische Daten
| CAS No. | 105-74-8 |
|---|---|
| Summenformel | C24H46O4 |
| Durchschnittliche Molmasse | 398,6 g/mol |
| Monoisotopische Masse | 398,33960995 g/mol |
| SMILES | CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC |
| InChIKey | YIVJZNGAASQVEM-UHFFFAOYSA-N |
| PubChem CID | 7773 |
| ChEBI | CHEBI:82479 |
| EC No. | 203-326-3 |
| DTXSID | DTXSID1059319 |
| Lokaler Name | Dilauroylperoxid |
Chemische & physikalische Eigenschaften
| XLogP | 10,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 23 |
| Schwere Atome | 28 |
| Formalladung | 0 |
| Komplexität | 321 |
| Stoffklassen | Other Classes -> Peroxides, Organic |
| Geruch | Faint pungent, soapy odorFaint odor |
| Geschmack | Tasteless |
| Dichte | 0.91 at 77 °F (USCG, 1999) - Less dense than waterwill float0.91 @ 25 °C (SOLID)0.9 g/cm³0.91 @25 °C0,91 g/cm3 |
| Color/Form | White coarse powderWhite flakes |
| Löslichkeit | Insol in waterslightly sol in alcSol in oils and most organic solventsSolubility in water: noneChloroform (Slightly), DMSO (Slightly, Sonicated)Soluble in oils and organic solvents. Slightly soluble in alcohol. Insoluble in water. |
| Siedepunkt | BOILING POINT: DECOMPOSES441.76°C (rough estimate) |
| Decomposition | Becomes shock sensitive on heating, and self-accelerating decomposition sets in at 49 °C. |
| Schmelzpunkt | 129 °F (USCG, 1999)49 °C49-57 °C53-57 °C(lit.) |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Physical Description | Lauroyl peroxide appears as a white solid with a faint soapy odor. Less dense than water and insoluble in water. Hence floats on water. Melting point 49 °C. Toxic by ingestion and inhalation. Strong skin irritant. Used as bleaching agent, drying agent for fats, oils and waxes, and as a polymerization catalyst.Dry PowderCBI[ICSC] White granules or crystals[MSDSonline]WHITE POWDER OR SOLID IN VARIOUS FORMS. |
| Stability/Shelf Life | STABLE IF NOT OVERHEATED |
| Dampfdichte | 13.7 (vs air) |
| Dampfdruck | 0Pa at 20℃ |
| Brechungsindex | 1.4460 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Powder |
| Farbe | White |
| Geruch | wh. coarse powd., faint odor, tasteless |
| BRN | 1804936 |
| InChI | 1S/C24H46O4/c1-3-5-7-9-11-13-15-17-19-21-23(25)27-28-24(26)22-20-18-16-14-12-10-8-6-4-2/h3-22H2,1-2H3 |
| InChIKey | YIVJZNGAASQVEM-UHFFFAOYSA-N |
| SMILES | CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC |
| LogP (Verteilungskoeffizient) | 10.3 |
| CAS Datenbank | 105-74-8(CAS DataBase Reference) |
| EPA chemische Informationen | Peroxide, bis(1-oxododecyl) (105-74-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH242: Heating may cause a fire [Danger Self-reactive substances and mixturesOrganic peroxides]P210, P234, P235, P240, P280, P370+P378, P403, P410, P411, P420, and P501 (click each P-code to see the statement)H242 (99.7%): Heating may cause a fire [Danger Self-reactive substances and mixtures |
|---|---|
| Regulatorische Informationen | Chemical: Peroxide, bis(1-oxododecyl)Regulation (EC) No 258/1997Peroxide, bis(1-oxododecyl) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Peroxide, bis(1-oxododecyl) 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: 17-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/2224Peroxide, bis(1-oxododecyl): Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| DOT-Kennzeichnung | Organic Peroxide |
| Brandgefahren | Behavior in Fire: Can increase the severity of a fire. Becomes sensitive to shock when hot. Containers may explode in a fire. May ignite or explode spontaneously if mixed with flammable materials. (USCG, 1999)Flammable. Risk of fire and explosion on contact with combustible substances or reducing agents. Risk of fire and explosion on warming. |
| Brandpotenzial | FIRE HAZARD: ORGANIC PEROXIDES CONTAIN SUFFICIENT AVAILABLE OXYGEN TO SUPPORT THEIR OWN COMBUSTION EVEN IN A DEFICIENCY OR ABSENCE OF ATMOSPHERIC OXYGEN. /PEROXIDES, ORGANIC/Can increase the severity of a fire. Becomes sensitive to shock when hot. Containers may explode in a fire. May ignite or explode spontaneously if mixed with flammable materials.Fire Precautions (In case of outbreak): Spray water hoses from areas as far as possible and free from possible explosion risk. If fire occurs in the vicinity of this agent, spray abundant water over the containers to protect from overheating. Clean up or salvage operations should not be attempted until the temperature has /dropped sufficiently/.STRONG OXIDIZING MATERIAL |
| Gesundheitsgefahren | Contact with liquid irritates eyes and skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999) |
| Gefahrenübersicht | A skin, eye, and respiratory tract irritant[ICSC] An irritant[MSDSonline] |
| FDA-Anforderungen | Dilauroyl peroxide is an indirect food additive for use only as a component of adhesives. |
| Reaktive Gruppe | Peroxides, Organic |
| EG-Einstufung | Symbol: OR: 7S: (2)-3/7-14-36-37/39 |
| UN-Einstufung | UN Hazard Class: 5.2 |
| Reactivity Alerts | Explosive |
| Reactivity Profile | LAUROYL PEROXIDE is an oxidizing agent. Can ignite organic materialshence a dangerous fire and explosion risk [Hawley]. Strongly reduced material such as sulfides, nitrides, and hydrides may react explosively. Vigorous reactions with other reducing agents. With charcoal sometimes ignites. [Bretherick, 5th ed., 1995, p. 1194]. |
| Brandbekämpfung | Fire Extinguishing Agents: Water, dry chemical, foam, or carbon dioxide (USCG, 1999)Use water in large amounts, water spray. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention . |
| Erste Hilfe | EYES: wash with plenty of water for 15 min. and get medical attention. |
| Sichere Lagerung | Fireproof. Separated from combustible substances and reducing agents. Cool. |
| Brandbekämpfungsverfahren | WATER, DRY CHEMICAL, FOAM, OR CARBON DIOXIDE.Combat fires from behind barrier. Flood discharge area with water. Cool exposed containers with water.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/ |
| Lagerbedingungen | Store in a cool, well-ventilated storage of noncombustible construction, distant from residences. Separate from other stocks, especially vulcanizing agents, easily oxidizable organic materials, and combustible materialavoid fire and sparks. Provide large-quantity storage room with cool sprinkler system. Protect containers against physical damage. Do not open containers in storage room. Do not place in glass-stopper or screw-capped containers because of possible explosion caused by frictional handling.STORAGE REQUIREMENTS: KEEP AS COOL AS POSSIBLE, BUT BELOW 27 °C. DO NOT ADD HOT MATERIAL.STORAGE REQUIREMENTS: BECAUSE OF THEIR INSTABILITY, MANY PEROXIDES ARE STORED AND HANDLED IN INERT VEHICLE SUCH AS DIMETHYL PHTHALATE. /PEROXIDES, ORG/STORAGE REQUIREMENTS: IN COMMERCIAL HANDLING, SHOCK-SENSITIVE PEROXIDES ARE DILUTED WITH SOME INACTIVE VEHICLE (EG DIMETHYL PHTHALATE). /PEROXIDES, ORGANIC/ |
| Reinigungsverfahren | Isolate and remove discharged material. Notify local health and pollution control agencies.IN CASE OF SPILLS, SUPPLY OF INACTIVE ABSORBENT MATERIAL (EG VERMICULITE) SHOULD BE AVAILABLE. /PEROXIDES, ORG/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/Dilute and drain into the sewer with abundant water. /Hydrogen peroxide/ |
| Freisetung ohne Brand | Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]: |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Verschüttetes entsorgen | Evacuate danger area! Consult an expert! Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Remove all ignition sources. Do NOT absorb in saw-dust or other combustible absorbents. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]: |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its aerosol. |
| Signs and Symptoms | Cough. Sore throat.Redness. Pain. |
| Human Toxicity Excerpts | PROLONGED INHALATION OF THE VAPORS /OF ORGANIC PEROXIDES/ RESULTS IN HEADACHE AND THROAT IRRITATION AND SPLASHES IN THE EYE CAN BE DAMAGING. PROLONGED SKIN CONTACT...MAY CAUSE IRRITATION AND BLISTERING. /ORGANIC PEROXIDES/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. ... /Peroxides, Organic and Inorganic/ |
| Carcinogen Classification | Lauroyl peroxideGroup 3: Not classifiable as to its carcinogenicity to humansVolume 36: (1985) Allyl Compounds, Aldehydes, Epoxides and Peroxides19991998 |
| Non-Human Toxicity Excerpts | ANIMAL TOXICITY STUDIES HAVE INDICATED...THAT EFFECTS OF ORGANIC PEROXIDES MAY BE CUMULATIVE. /PEROXIDES, ORG/...HAS BEEN SHOWN TO BE NONINJURIOUS WHEN APPLIED TO RABBIT EYES IN POWDER FORM.MALE RATS GIVEN LAUROYL PEROXIDE IN EQUIV TO 0.02 OR 0.004 LD50 & LD33 WITH FOOD FOR 4 MO. DECR HEMOGLOBIN & ERYTHROCYTES, INCR RETICULOCYTES IN PERIPHERAL BLOOD, INCR METHEMOGLOBIN FORMATION, DECR BLOOD SULFHYDRYL GROUP & BLOOD PEROXIDASE.After a single topical application of either 10, 20, or 40 mg of lauroyl peroxide...on the dorsal mouse skin, the epidermal thickness increased markedly. No major inflammatory or vascular alterations were noted. ... Lauroyl peroxide-induced hyperplasia was characterized by a sustained production of dark basal keratinocytes, which constituted approximately 10% of the basal cell population during the first week after single topical application. Although /lauroyl peroxide/ was inactive either as an initiator or as a complete carcinogen, it was...effective... when used as a skin tumor promoter in a 2-stage carcinogenesis protocol.For more Non-Human Toxicity Excerpts (Complete) data for DILAUROYL PEROXIDE (8 total), please visit the HSDB record page. |
| Populations at Special Risk | Individuals with eye, skin, and chronic respiratory diseases /may be/ at an increased risk. /Hydrogen peroxide/ |
| Evidence for Carcinogenicity | Evaluation: No epidemiological data relevant to the carcinogenicity of lauroyl peroxide were available. There is inadequate evidence in experimental animals for the carcinogenicity of lauroyl peroxide. Overall evaluation: Lauroyl peroxide is not classifiable as to its carciogenicity to humans (Group 3). |
| Antidote and Emergency Treatment | TREATMENT: PROMPT WASHING OF AFFECTED AREAS IS ESSENTIAL.REMOVE CONTAMINATED CLOTHING & SHOES. FLUSH AFFECTED AREAS WITH... WATER. IF IN EYES, HOLD EYELIDS OPEN & FLUSH WITH... WATER. IF SWALLOWED & VICTIM IS CONSCIOUS, HAVE VICTIM DRINK WATER OR MILK & HAVE VICTIM INDUCE VOMITING. IF SWALLOWED & VICTIM IS UNCONSCIOUS OR HAVING CONVULSIONS, DO NOTHING EXCEPT KEEP VICTIM WARM.Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool .... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic peroxides/Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic peroxides/Peroxides should be washed promptly from the skin to prevent irritation. In the case of eye contact, the eyes should be flushed immediately with large amounts of water, and medical attention should be obtained. ... /Peroxides, Organic and Inorganic/ |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3106 5.2 |
| Zollcode | 29159000 |
| RTECS-Nr. | OF2625000 |
| R-Sätze (R) | 7 |
| Gefahrensymbole | O |
| Sicherheitshinweise (S) | 14-3/7-36/37/39-14A-37/39-36 |
| Gefahrenklasse | 5.2Org. Perox. D |
| Verpackungsgruppe | II |
| Lagerklasse | 5.2 - Organic peroxides and self-reacting hazardous materials |
| Gefahrstoffdaten | 105-74-8(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 112°C |
Anwendungen & Verwendung
Verwenden
Dilauroyl peroxide is produced by reaction of lauroyl chloride with sodium peroxide. Its major use is as an initiator for vinyl chloride. It is used as a polymerization agent in the plastics industry and as a curing agent for rubber. It has also been used as a burnout agent for acetate yarns. The pharmaceutical industry uses it in topical creams in combination with antibiotics for acne treatment .
Herstellung & Synthese
synthetische
Dilauroyl peroxide is the symmetrical peroxide of lauric acid. It is produced by treating lauroyl chloride with hydrogen peroxide in the presence of base:2C11H23COCl + H2O2+ 2NaOH → (C11H23CO2)2 + 2HCl