Lauroyl peroxide

HCID 7773CAS 105-74-8

Basic information

Standard SMILES
CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC
InChIKey
YIVJZNGAASQVEM-UHFFFAOYSA-N
Molecular formula
C24H46O4
Average molar mass
398.6 g/mol
Monoisotopic mass
398.33960995

Overview

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.

Names & identifiers

Preferred name
Lauroyl peroxide
IUPAC
dodecanoyl dodecaneperoxoate
English name
Lauroyl peroxide
Molecular formula
C24H46O4
Molecular weight
398.62

Names & synonyms

Lauroyl peroxide105-74-8DILAUROYL PEROXIDEAlperox CPeroxide, bis(1-oxododecyl)LaurydolDodecanoyl peroxideLauroxPeroxyde de lauroyleLYP 97Laurox QPeroxide, didodecanoyl
Show more names
LPOlauroylLAURYL PEROXIDEDodecanoic peroxyanhydridedodecanoyldilaurylperoxide
LYP 97FPeroxide, bis(1-oxododecyl)-Luperox LP83TLB4N1D5PEROYL LNSC-670DTXSID1059319RefChem:152523

Database identifiers

CAS
105-74-8
PubChem CID
7773
DTXSID
DTXSID1059319
ChEBI
CHEBI:82479
UNII
83TLB4N1D5
EC Number
203-326-3
Nikkaji
J2.853C

Properties

Computed structural properties

XLogP
10.5
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
23
Heavy atoms
28

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Peroxides, Organic
Odor · 2 items

Faint pungent, soapy odor

Faint odor

TasteTasteless
Density · 4 items

0.91 at 77 °F (USCG, 1999) - Less dense than water; will float

0.91 @ 25 °C (SOLID)

0.9 g/cm³

0.91 @25 °C

Color/Form · 2 items

White coarse powder

White flakes

Solubility · 3 items

Insol in water; slightly sol in alc

Sol in oils and most organic solvents

Solubility in water: none

Physicochemical properties

Melting point
53 · 53-57 °C(lit.)
Boiling point
441.76 °C · 441.76°C (rough estimate)
Density
0 · 0,91 g/cm3
vapor density
13.7 · 13.7 (vs air)
vapor pressure
0 Pa · 0Pa at 20℃
refractive index
1.446 · 1.4460 (estimate)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H242: Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]

P210, P234, P235, P240, P280, P370+P378, P403, P410, P411, P420, and P501 (click each P-code to see the statement)

Danger

H242 (99.7%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]

P210, P234, P235, P240, P280, P370+P378, P403, P410, P411, P420, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 5 items

Chemical: Peroxide, bis(1-oxododecyl)

Regulation (EC) No 258/1997

Peroxide, 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/2224

Peroxide, 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 LabelOrganic Peroxide
Fire Hazards · 2 items

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.

Fire Potential · 4 items

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

Health HazardsContact with liquid irritates eyes and skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)
Hazards SummaryA skin, eye, and respiratory tract irritant; [ICSC] An irritant; [MSDSonline]

Safety & protection

Fire Fighting · 2 items

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.

First Aid Measures · 4 items

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 .

First AidEYES: wash with plenty of water for 15 min. and get medical attention.
Safe StorageFireproof. Separated from combustible substances and reducing agents. Cool.
Fire Fighting Procedures · 3 items

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/

Storage Conditions · 4 items

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 material; avoid 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/

Toxicology

Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol.
Signs and Symptoms · 3 items

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

Human Toxicity Excerpts · 2 items

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 · 5 items

Lauroyl peroxide

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 36: (1985) Allyl Compounds, Aldehydes, Epoxides and Peroxides

1999

1998

Non-Human Toxicity Excerpts · 5 items

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 RiskIndividuals with eye, skin, and chronic respiratory diseases /may be/ at an increased risk. /Hydrogen peroxide/

Regulatory information

FDA RequirementsDilauroyl peroxide is an indirect food additive for use only as a component of adhesives.

Safety data

PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
1
tsca
TSCA listed
rtecs
OF2625000
ridadr
UN 3106 5.2
hs_code
29159000

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as a bleaching agent, drying agent (fats, oils, and waxes), polymerization catalyst, curing agent (rubber and resins), burn-out agent for acetate yarns; and topical drug for acne; [HSDB]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

Bleaching agent, intermediate, and drying agent for fats, oils and waxes; polymerization catalyst.

...an initiator for vinyl chloride...a polymerization agent in the plastics industry and as a curing agent for rubber...burn-out agent for acetate yarns...pharmaceutical industry uses it in topical creams in combination with antibiotics for acne treatment.

USED AS BLEACH FOR FLOUR, VEGETABLE OILS, FATS AND WAXES; AS POLYMERIZATION AGENT IN PLASTICS INDUSTRY

AS CURING AGENT FOR RUBBER; AS BURN-OUT AGENT FOR ACETATE YARNS; IN COSMETICS & PHARMACEUTICALS INDUSTRY

U.S. Production · 3 items

2023: <75,000 lb

(1977) AT LEAST 4.54X10+7 G

(1982) 1.20X10+8 G

Industry UsesCBI
Methods of Manufacturing · 3 items

PREPN: FORMATION OF THE PEROXIDES IS BY DIRECT ATMOSPHERIC OXIDATION, BY PHOTOSENSITIZED OXYGEN OXIDATION, OR BY ACID-CATALYZED HYDROGEN PEROXIDE ON THE APPROPRIATE C STRUCTURE. /ORG PEROXIDES/

REACTION OF LAUROYL CHLORIDE WITH SODIUM PEROXIDE

Reaction of lauroyl chloride with hydrogen peroxide

Formulations/Preparations · 5 items

97-98%: dry or wetted with water.

Grades: technical (about 95%).

Laurox

LAUROX Q

For more Formulations/Preparations (Complete) data for DILAUROYL PEROXIDE (7 total), please visit the HSDB record page.

General Manufacturing Information · 3 items

CBI

Peroxide, bis(1-oxododecyl): ACTIVE

Use: Composite material for dental fillings

Applications · 4 items

UsesDilauroyl 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 .

UsesLauroyl peroxide acts as a bleaching agent, drying agent for fats, oils and waxes. Further, it serves as a polymerization initiator as well as vulcanizing agent. In addition to this, it plays an important role for high-pressure polyethylene and food used in bleaching agent.

UsesLauroyl peroxide is used as an initiatorfor free-radical polymerization in makingpolyvinyl chloride. Lauroyl peroxide constitutesabout 4% of all organic peroxides consumptionin the United States.

General DescriptionDilauroyl 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.

Preparation methods

PreparationDilauroyl 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

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]
武汉欣扬瑞和化学科技有限公司13720274133 · [email protected]
武汉欣扬瑞和化学科技有限公司18171205315; 18171205315 · [email protected]

Additional notes

DefinitionChEBI: Lauroyl peroxide is a dicarboxylic acid.

Related reactions

21 records

Linked notes

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