80-15-9 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 80-15-9 differently. You can refer to the following data:
1. colourless liquid
2. Cumene hydroperoxide, an organic peroxide, is a colorless to pale yellow to green liquid. Mild odor.
Uses
Different sources of media describe the Uses of 80-15-9 differently. You can refer to the following data:
1. Production of acetone and phenol; polymerization catalyst, particularly in redox systems, used for
rapid polymerization.
2. Cumene hydroperoxide is used for the manufactureof acetone and phenols; for studyingthe mechanism of NADPH-dependent lipidperoxidation; and in organic syntheses.
3. Cumene hydroperoxide is used in the preparation of polystyrene nanocapsules. It acts as a curing agent for polyester resins and as an oxidizer in organic chemical reactions. It serves as an initiator for radical polymerization especially for acrylate and methacrylate monomers. It also employed as an intermediate in the cumene process for developing phenol and acetone from benzene and propene. Further, it is used as an epoxidation reagent for allylic alcohols and fatty acid esters. In addition to this, it is also used to prepare methylstyrene, acetophenone and cumyl alcohol.
Definition
ChEBI: A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.
General Description
Colorless to light yellow liquid with a sharp, irritating odor. Flash point 175°F. Boils at 153°C and at 100°C at the reduced pressure of 8 mm Hg. Slightly soluble in water and denser than water. Hence sinks in water. Readily soluble in alcohol, acetone, esters, hydrocarbons, chlorinated hydrocarbons. Toxic by inhalation and skin absorption. Used in production of acetone and phenol, as a polymerization catalyst, in redox systems.
Air & Water Reactions
Slightly soluble in water and oxidized in air at approximately 130°C.
Reactivity Profile
Cumyl hydroperoxide is a strong oxidizing agent. May react explosively upon contact with reducing reagents Violent reaction occurs upon contact with copper, copper alloys, lead alloys, and mineral acids. Contact with charcoal powder gives a strong exothermic reaction. Decomposes explosively with sodium iodide [Chem. Eng. News, 1990, 68(6), 2]. Can be exploded by shock or heat [Sax, 2 ed., 1965, p. 643]. May ignite organic materials.
Hazard
Toxic by inhalation and skin absorption.
Strong oxidizing agent; may ignite organic materials.
Health Hazard
Different sources of media describe the Health Hazard of 80-15-9 differently. You can refer to the following data:
1. Cumene hydroperoxide is a mild to moderateskin irritant on rabbits. Subcutaneousapplication exhibited a strong delayed reactionwith symptoms of erythema and edema(Floyd and Stockinger 1958). Strong solutionscan irritate the eyes severely, affectingthe cornea and iris.Its toxicity is comparable to that of tertbutylhydroperoxide. The toxic routes areingestion and inhalation. The acute toxicitysymptoms in rats and mice were muscleweakness, shivering, and prostration.Oral administration of 400 mg/kg resulted inexcessive urinary bleeding in rats.LD50 value, oral (rats): 382 mg/kgLD50 value, intraperitoneal (rats): 95 mg/kgAlthough cumene hydroperoxide is toxic,its pretreatment may be effective against thetoxicity of hydrogen peroxide. In humans, itstoxicity is low.Cumene hydroperoxide is mutagenic andtumorigenic (NIOSH 1986). It may causetumors at the site of application. In mice,skin and blood tumors have been observed.Its cancer-causing effects on humans are notknown.
2. Inhalation of vapor causes headache and burning throat. Liquid causes severe irritation of eyes; on skin, causes burning, throbbing sensation, irritation, and blisters. Ingestion causes irritation of mouth and stomach.
Fire Hazard
Flammable; highly reactive and oxidizing.
Flash point 79°C (174.2°F); vapor density
5.2 (air= 1); autoignition temperature not
reported; self-accelerating decomposition
temperature 93°C (199.4°F).
When exposed to heat or flame, it may
ignite and/or explode. A 91–95% concentration
of cumene hydroperoxide decomposes
violently at 150°C (302°F) (NFPA 1986).
Duswalt and Hood (1990) reported violent
decomposition when this compound mixed
accidentally with a 2-propanol solution of
sodium iodide.
It forms an explosive mixture with air.
The explosive concentration range is not
reported. Hazardous when mixed with easily
oxidizable compounds. Fire-extinguishing
agent: water from a sprinkler or fog nozzle
from an explosion-resistant location.
Flammability and Explosibility
Nonflammable
Potential Exposure
Cumene hydroperoxide is used as polymerization initiator, curing agent for unsaturated polyester resins and cross-linking agent; as an intermediate in the process for making phenol plus acetone from cumene.
storage
Cumene hydroperoxide is stored in a cool,dry and well-ventilated area isolated fromother chemicals. It should be protectedagainst physical damage. It may be shippedin wooden boxes with inside glass or earthenwarecontainers or in 55-gallon metal drums.
Shipping
UN3109 Organic peroxide type F, liquid, Hazard Class: 5.2; Labels: 5.2-Organic peroxide, Technical Name Required.
Purification Methods
Purify the hydroperoxide by adding 100mL of 70% material slowly and with agitation to 300mL of 25% NaOH in water, keeping the temperature below 30o. The resulting crystals of the sodium salt are filtered off, washed twice with 25 mL portions of *benzene, then stirred with 100mL of *benzene for 20minutes. After filtering off the crystals and repeating the washing, they are suspended in 100mL of distilled water and the pH is adjusted to 7.5 by addition of 4M HCl. The free hydroperoxide is extracted into two 20mL portions of n-hexane, and the solvent is evaporated under vacuum at room temperature, the last traces being removed at 40-50o/1mm [Fordham & Williams Canad J Res 27B 943 1949]. Petroleum ether, but not diethyl ether, can be used instead of *benzene, and powdered solid CO2 can replace the 4M HCl. [Beilstein 6 IV 3221.] The material is potentially EXPLOSIVE.
Incompatibilities
The pure material is reported to explode on heating at elevated temperatures (various values given are 50°, 109, 150°C) or in strong sunlight. The substance is a strong oxidizer; reacts violently with combustible and reducing agents, causing fire and explosion hazard. Contact with metallic salts of cobalt, copper or lead alloys; mineral acids; bases; and amines may lead to violent decomposition. Vapor forms an explosive mixture with air. May accumulate static electrical charges, and may cause ignition of its vapors.
Check Digit Verification of cas no
The CAS Registry Mumber 80-15-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 80-15:
(4*8)+(3*0)+(2*1)+(1*5)=39
39 % 10 = 9
So 80-15-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H12.H2O2/c1-8(2)9-6-4-3-5-7-9;1-2/h3-8H,1-2H3;1-2H
80-15-9Relevant articles and documents
Insights into the mechanism of cumene peroxidation using supported gold and silver nanoparticles
Crites, Charles-Oneil L.,Hallett-Tapley, Geniece L.,Frenette, Mathieu,Gonzalez-Bejar, Maria,Netto-Ferreira,Scaiano
, p. 2062 - 2071 (2013)
Due to the considerable industrial implications, an in-depth study of cumene peroxidation using supported gold and silver nanoparticles was carried out to gain more insight into the mechanism of this reaction. Supported gold nanoparticles were found to ef
Oxidation of cumene in the presence of high concentrations of ascorbic acid
Smirnova,Efimova,Opeida
, p. 427 - 430 (2011)
Initiated oxidation of cumene by oxygen in the presence of ascorbic acid was studied.
A highly efficient transformation from cumene to cumyl hydroperoxide via catalytic aerobic oxidation at room temperature and investigations into solvent effects, reaction networks and mechanisms
Chen, Chong,Ji, Lijun,Lu, Qiuting,Shi, Guojun,Yuan, Enxian,Zhou, Hongyu
, (2021/12/04)
Cumyl hydroperoxide (CHP) is an important intermediate for the production of phenol/acetone, but suffers from severe reaction conditions and a low yield industrially. Here, an efficient transformation from cumene to CHP was developed. Different solvents were modulated for cumene oxidation catalyzed by NHPI/Co, and reaction network and mechanisms were investigated methodically. Hexafluoroisopropanol (HFIP) markedly promoted the transformation from cumene to CHP compared to other solvents at room temperature. A cumene conversion high up to 64.3% were observed with a selectivity to CHP of 71.7%. The solvent HFIP exhibited a significant promotion on cumene oxidation due to its contribution to the enhancement of the concentration of PINO radicals. Moreover, cumyl, cumyl oxyl and methyl radicals were captured by TEMPO and analyzed by HRMS, and the reaction paths and mechanisms from cumene to products were inferred. The preparation method discovered in this work may open an access to the production of CHP.
LIGHT INDUCED CATALYTIC C-H OXYGENATION OF ALKANES
-
Paragraph 00201; 00207; 00212; 00217, (2021/04/02)
A method of oxygenating a benzylic C-H bond is provided. The method comprises light induced activation of an initiator and subsequent reaction with oxygen, resulting in the formation of free radicals. Subsequently, free radicals catalyze the reaction of the benzylic C-H bond with oxygen, thereby forming an oxygenated compound.
The influence of Fe(III) acetylacetonate and o-phenanthroline towards improvement of NHPI-catalyzed cumene oxidation
Babushkin, D. E.,Karmadonova, I. E.,Kuznetsova, L. I.,Kuznetsova, N. I.
, (2021/10/19)
Cumene hydroperoxide (CHP) is the most important product or intermediate in the oxidative processing of cumene. In the present study, cooperative action of NHPI catalyst with Fe(acac)3/Phen additives in oxidation of cumene has been described in terms of oxidation rate and selectivity for products, notably CHP, under variable conditions. The oxidation characteristics were influenced by promoting additives, the main function of which was to generate an active PINO radical. An abundance of the additives might enhance the non-selective conversion of intermediates and decomposition of CHP, which led to a decrease in CHP selectivity. The addition of 0.0003 mol% Fe(acac)3 was sufficient to initiate NHPI catalyzed fast cumene oxidation and very selective CHP production at 50 °°C. Phen showed an impressive multifaceted effect, as the increase in its amount initially lowered the CHP selectivity and then increased to 95% with a large excess of Phen over Fe(acac)3. That was due to the different ability of iron complexes of various compositions to react to NHPI and to CHP. UV-VIZ spectroscopy and DFT calculation was used to elucidate assistance of Phen in reduction of Fe(acac)3 with NHPI and creation of FeII/FeIII –Phen2or3 complexes as reversible single-electron carriers upon catalysis by NHPI. In addition, the selective formation of CHP contributes to the resistance of NHPI to degradation during catalysis.