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Cumyl hydroperoxide

Cumyl hydroperoxide
Cumyl hydroperoxide structure
CAS No.
80-15-9
Chemical Name:
Cumyl hydroperoxide
Synonyms
CHP-5;HPC-9;CHP-158;Hyperiz;Percumyl H;Trigonox?K;Trignox K80;Aztec CHP-80;Kayacumene H;LUPEROX CU90
CBNumber:
CB7203705
Molecular Formula:
C9H12O2
Formula Weight:
152.19
MOL File:
80-15-9.mol

Cumyl hydroperoxide Properties

Melting point:
-30 °C
Boiling point:
100-101 °C8 mm Hg(lit.)
Density 
1.05 g/mL at 25 °C(lit.)
vapor density 
5.4 (vs air)
vapor pressure 
<0.03 mm Hg ( 20 °C)
refractive index 
n20/D 1.5230
Flash point:
192 °C
storage temp. 
2-8°C
pka
pK1:12.60 (25°C)
Water Solubility 
Slightly soluble
BRN 
1908117
Exposure limits
No exposure limit is set. On the basis of its irritant properties, a ceiling limit of 2 mg/m3 (0.3 ppm) is recommended.
Stability:
Stable. combustible. Strong oxidizer. Incompatible with a variety of organic materials, reacting vigorously or violently with acids, reducing agents, many metals, strong alkalies. Heat sensitive, decomposing explosively.
CAS DataBase Reference
80-15-9(CAS DataBase Reference)
NIST Chemistry Reference
Hydroperoxide, 1-methyl-1-phenylethyl(80-15-9)
EPA Substance Registry System
Hydroperoxide, 1-methyl-1-phenylethyl(80-15-9)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
Hazard Codes  O,T,N
Risk Statements  7-21/22-23-34-48/20/22-51/53-66-65-10-37
Safety Statements  14-3/7-36/37/39-45-50-61-14A-26-62-47-7
RIDADR  UN 3109 5.2
WGK Germany  3
RTECS  MX2450000
TSCA  Yes
HazardClass  5.2
PackingGroup  II
HS Code  29096000
Hazardous Substances Data 80-15-9(Hazardous Substances Data)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H226 Flammable liquid and vapour Flammable liquids Category 3 Warning
H227 Combustible liquid Flammable liquids Category 4 Warning P210, P280, P370+P378, P403+P235,P501
H242 Heating may cause a fire Self-reactive substances and mixtures; and Organic peroxides Type C, D,Type E, F
Type G
Danger
Warning
P210, P220, P234, P280, P370+P378,P403+P235, P411, P420, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H304 May be fatal if swallowed and enters airways Aspiration hazard Category 1 Danger
H312 Harmful in contact with skin Acute toxicity,dermal Category 4 Warning P280,P302+P352, P312, P322, P363,P501
H314 Causes severe skin burns and eye damage Skin corrosion/irritation Category 1A, B, C Danger P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H341 Suspected of causing genetic defects Germ cell mutagenicity Category 2 Warning P201,P202, P281, P308+P313, P405,P501
H371 May cause damage to organs Specific target organ toxicity, single exposure Category 2 Warning P260, P264, P270, P309+P311, P405,P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
Precautionary statements:
P201 Obtain special instructions before use.
P202 Do not handle until all safety precautions have been read and understood.
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P220 Keep/Store away from clothing/…/combustible materials.
P234 Keep only in original container.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P271 Use only outdoors or in a well-ventilated area.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P391 Collect spillage. Hazardous to the aquatic environment
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P370+P378 In case of fire: Use … for extinction.
P405 Store locked up.
P410 Protect from sunlight.
P403+P233 Store in a well-ventilated place. Keep container tightly closed.

NFPA 704

Diamond Hazard Value Description
2
1 4
OX
Health   1 Exposure would cause irritation with only minor residual injury (e.g. acetone, sodium bromate, potassium chloride)
Flammability   2 Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur and multiple finely divided suspended solids that do not require heating before ignition can occur. Flash point between 37.8 and 93.3 °C (100 and 200 °F). (e.g. diesel fuel, sulfur)
Instability   4 Readily capable of detonation or explosive decomposition at normal temperatures and pressures (e.g. nitroglycerin,chlorine dioxide, nitrogen triiodide)
Special   OX

(NFPA, 2010)

Cumyl hydroperoxide price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 247502 Cumene hydroperoxide technical grade, 80% 80-15-9 5g $24.1 2018-11-13 Buy
Sigma-Aldrich 247502 Cumene hydroperoxide technical grade, 80% 80-15-9 100g $27.3 2018-11-13 Buy
TCI Chemical C2223 Cumene Hydroperoxide (contains ca. 20% Aromatic Hydrocarbon) 80-15-9 100g $28 2018-11-22 Buy
Alfa Aesar L06866 Cumene hydroperoxide, tech. 80% 80-15-9 100g $28.5 2018-11-13 Buy
Alfa Aesar L06866 Cumene hydroperoxide, tech. 80% 80-15-9 500g $73.5 2018-11-13 Buy

Cumyl hydroperoxide Chemical Properties,Uses,Production

Chemical Properties

colourless liquid

Chemical Properties

Cumene hydroperoxide, an organic peroxide, is a colorless to pale yellow to green liquid. Mild odor.

Uses

Production of acetone and phenol; polymerization catalyst, particularly in redox systems, used for rapid polymerization.

Uses

Cumene hydroperoxide is used for the manufactureof acetone and phenols; for studyingthe mechanism of NADPH-dependent lipidperoxidation; and in organic syntheses.

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

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/kg
LD50 value, intraperitoneal (rats): 95 mg/kg
Although 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.

Health Hazard

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.

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.

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.

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.

Cumyl hydroperoxide Preparation Products And Raw materials

Raw materials

Preparation Products


Cumyl hydroperoxide Suppliers

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