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Diacetyl peroxide

HCID 8040
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
110-22-5
Standard SMILES
CC(=O)OOC(C)=O
InChIKey
ZQMIGQNCOMNODD-UHFFFAOYSA-N
Molecular formula
C4H6O4
Average molar mass
118.09 g/mol
Monoisotopic mass
118.02660867

Overview

Acetyl peroxide solution, [<= 25% peroxide] is a colorless liquid with a sharp odor. Consists of a solution of acetyl peroxide in dimethyl phthalate. Sinks in water.

Names & identifiers

Preferred name
Diacetyl peroxide
IUPAC
acetyl ethaneperoxoate
English name
Acetyl peroxide
Molecular formula
C4H6O4
Molecular weight
118.09

Names & synonyms

Acetyl peroxideDIACETYL PEROXIDEPeroxide, diacetyl110-22-5DiacetylperoxidePeroyl AHSDB 298NSC 669EINECS 203-748-8UNII-FDU6Y8075ABRN 1753975FDU6Y8075A
Show more names
peroylaDiacetylperoxidethanoyl peroxideperoxide,diacetylethanoyl ethaneperoxoateperacetic acid acetyl ester
NSC-669DIACETYL PEROXIDE [HSDB]DTXSID40593844-02-00-00392 (Beilstein Handbook Reference)RefChem:132556DTXCID7033157203-748-8acetyl ethaneperoxoate

Database identifiers

CAS
110-22-5
PubChem CID
8040
DTXSID
DTXSID4059384
UNII
FDU6Y8075A
EC Number
203-748-8
Nikkaji
J2.448A

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
52.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
8
Formal charge
0
Complexity
92.6

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Peroxides, Organic

Flammable agents - 2nd degree

SpringerMaterials PropertiesChemical shift
OdorStrong, pungent odor
Density · 5 items

1.2 at 68 °F (USCG, 1999) - Denser than water; will sink

1.18 @ 20 °C

STRONG PUNGENT ODOR; SHOCK-SENSITIVE CRYSTALS MAY FORM BELOW 17 °F; VAPOR DENSITY: 4.07 /25% SOLN/

DENSITY: 1.18 /25% SOLN/

1.18 @25 °C

Color/Form · 2 items

Colorless crystals

NEEDLES FROM ETHER, LEAVES

Solubility · 2 items

Slightly soluble in cold water

Very soluble in ethanol and ethyl ether

Flash Point · 3 items

113 °F (USCG, 1999)

113 °F (NFPA, 2010)

113 °F OC

Boiling Point63 °C @ 21 mm Hg
Melting Point · 3 items

17 °F (USCG, 1999)

30 °C

30 °C

Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 3 items

Acetyl peroxide solution, [<= 25% peroxide] is a colorless liquid with a sharp odor. Consists of a solution of acetyl peroxide in dimethyl phthalate. Sinks in water.

The pure compound consists of colorless crystals melting at 30 °C. Soluble in alcohol and ether. Often transported as a 25% solution in dimethyl phthalate for use as an initiator and catalyst.

Colorless solid; Available as 25% solution in dimethyl phthalate; [Hawley] mp = 30 deg C; [ChemIDplus]

Stability/Shelf LifeHIGHLY UNSTABLE /ORG PEROXIDES/

Physicochemical properties

Melting point
30 °C · 30°C
Boiling point
140.59 °C · 140.59°C (rough estimate)
Density
1.0887 · 1.0887 (rough estimate)
refractive index
1.45 · 1.4500 (estimate)
Stability
Explosive. May explode if heated, or in contact with combustible materials. The pure material should not be handled by untrained persons. Unstable as the pure material. Incompatible with organic materials.
LogP
-0.038 · -0.038 (est)
Indirect Additives used in Food Contact Substances
DIACETYL PEROXIDE
FDA 21 CFR
175.105 · 175.105; 176.170
EWG's Food Scores
1 · 1
FDA UNII
6 Y8075A · FDU6Y8075A
EPA Substance Registry System
Peroxide, diacetyl (110-22-5)
RIDADR
3115 · 3115
TSCA
TSCA listed
HazardClass
5.2 · 5.2
PackingGroup
II
Hazardous Substances Data
110 · 110-22-5(Hazardous Substances Data)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory Information · 2 items

Chemical: Peroxide, diacetyl

The 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.)

DOT Label · 2 items

Organic Peroxide

Organic Peroxide

Fire Hazards · 2 items

Behavior in Fire: May explode. Burns with accelerating intensity. (USCG, 1999)

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

Fire Potential · 2 items

DANGEROUS, BY SPONTANEOUS CHEMICAL REACTION. A POWERFUL OXIDIZING AGENT; CAN CAUSE IGNITION OF ORGANIC MATERIALS ON CONTACT.

AN OXIDIZING MATERIAL. SENSITIVE TO HEAT & SHOULD NOT BE SUBJECTED TO TEMP ABOVE 90 °F; SELF-ACCELERATING DECOMP TEMP, 120 °F. /25% SOLN/

Health Hazards · 2 items

Contact with liquid causes irritation of eyes and skin. If ingested, irritates mouth and stomach. (USCG, 1999)

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

Hazards Summary · 1 item

A tumorigen and severe eye irritant; [RTECS] A moderate fire and severe explosion hazard; A strong skin and eye irritant; [Hawley] A skin, eye, and respiratory tract irritant; 2 drops of a 30% solutions caused severe corneal damage when tested in rabbits; [HSDB] May cause severe injury or burns to skin and eyes; [CAMEO]

FDA RequirementsDiacetyl peroxide is an indirect food additive for use only as a component of adhesives.
Reactive Group · 2 items

Peroxides, Organic

Peroxides, Organic

Reactivity Alerts · 2 items

Strong Oxidizing Agent

Explosive

Reactivity Profile · 2 items

Peroxides, such as ACETYL PEROXIDE, are good oxidizing agents. Organic compounds can ignite on contact with concentrated peroxides. Strongly reduced material such as sulfides, nitrides, and hydrides may react explosively with peroxides. There are few chemical classes that do not at least produce heat when mixed with peroxides. Many produce explosions or generate gases (toxic and nontoxic). Generally, dilute solutions of peroxides (<70%) are safe, but the presence of a catalyst (often a transition metal such as cobalt, iron, manganese, nickel, or vanadium) as an impurity may even then cause rapid decomposition, a buildup of heat, and even an explosion. Solutions of peroxides often become explosive when evaporated to dryness or near-dryness.

Pure DIACETYL PEROXIDE, a solid, presents a severe explosion hazard. Unpredictably shock sensitive. Five grains detonated violently while being removed from an ice chest [Chem. Eng. News 26:3197(1948)]. May explode violently in contact with ether or any volatile solvent. A 5-gram portion in ether detonated while being carried [Chem. Eng. News 27:175(1949)]. The 25% solution in dimethyl phthalate is less dangerous, but still a strong oxidizing agent that presents a moderate fire risk [Hawley].

DOT Hazard Classification · 4 items

Acetyl peroxide, solid, or with more than 25 percent in solution

Forbidden explosives/materials (49 eCFR § 173.54/§ 173.21)

Diacetyl peroxide, solid, or with more than 25 percent in solution

Forbidden explosives/materials (49 eCFR § 173.54/§ 173.21)

Air and Water Reactions · 2 items

No rapid reaction with air. No rapid reaction with water.

No rapid reaction with air. No rapid reaction with water.

Safety & protection

Fire Fighting · 2 items

Fire Extinguishing Agents: Water, dry chemical, carbon dioxide (USCG, 1999)

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

First Aid · 2 items

EYES: wash with plenty of water and get medical attention.

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

Firefighting HazardsIF CONTAMINATED CLOTHING IGNITES, USE WATER TO EXTINGUISH; SMOTHERING FIRE WITH BLANKET IS INEFFECTIVE. /25% SOLN/
Fire Fighting Procedures · 3 items

FIGHT...WITH WATER FROM EXPLOSION-RESISTANT LOCATION. IN ADVANCED OR MASSIVE FIRES...AREA SHOULD BE EVACUATED. IF FIRE OCCURS IN VICINITY OF THIS MATERIAL WATER SHOULD BE USED TO KEEP CONTAINERS COOL. CLEAN-UP & SALVAGE OPERATIONS SHOULD NOT BE ATTEMPTED UNTIL ALL...COOLED COMPLETELY. /25% SOLN/

FIREFIGHTING METHOD: WATER, DRY CHEM, CARBON DIOXIDE. /25% SOLN/

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 · 2 items

PROTECT AGAINST PHYSICAL DAMAGE. STORE ONLY IN DETACHED, ISOLATED NONCOMBUSTIBLE BUILDING ERECTED FOR THIS PURPOSE & USED EXCLUSIVELY FOR THIS MATERIAL. DO NOT STORE SOLID OR PASTE PEROXIDES IN SAME BUILDING... NO ELECTRICAL INSTALLATION, OPEN FLAMES OR OTHER SOURCES OF IGNITION PERMITTED IN STORAGE BUILDING. /25% SOLN/

STORAGE BUILDING TEMP MUST BE MAINTAINED IN RANGE OF 32 °F TO 90 °F. STORE ONLY IN ORIGINAL CONTAINERS WITH SPECIAL VENTING CAPS. DO NOT OPEN CONTAINERS IN STORAGE BUILDING. PROVIDE SUPPLY OF NONCOMBUSTIBLE ABSORBENT MATERIAL SUCH AS VERMICULITE OR PERLITE TO SOAK UP ANY ACCIDENTAL SPILLAGE & REMOVE... /25% SOLN/

Cleanup Methods · 4 items

IN EVENT OF SPILLAGE...SPILLED MATERIAL SHOULD BE ABSORBED...WITH NONCOMBUSTIBLE ABSORBENT, SUCH AS VERMICULITE. SWEEP UP & PLACE IN PLASTIC CONTAINER FOR IMMEDIATE DISPOSAL. DO NOT USE SPARK-GENERATING METALS OR CELLULOSIC MATERIALS (PAPER, WOOD, ETC) FOR SWEEPING UP OR HANDLING SPILLED MATERIAL. /25% SOLN/

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/

Nonfire Spill Response · 2 items

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

Disposal Methods · 1 item

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.

Preventive Measures · 1 item

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 · 2 items

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

Protective Action Criteria (PAC) · 3 items

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

Personal Protective Equipment (PPE) · 4 items

Protective goggles; rubber apron and gloves. (USCG, 1999)

Excerpt from ERG Guide 148 [Organic Peroxides (Heat and Contamination Sensitive / Temperature Controlled)]:

A FACE SHIELD & RUBBER GLOVES SHOULD BE WORN WHEN HANDLING THE SUBSTANCE, & A SAFETY SHIELD OR HOOD DOOR SHOULD BE IN FRONT OF APPARATUS CONTAINING IT.

Persons handling peroxides should use safety glasses with side shields, goggles or face shield for eye protection. Emergency eyewash facilities should be provided. Gloves, aprons and other protective clothing as necessary should be used to prevent skin contact. Clothing and equipment that generate static electricity should be avoided. Smoking should be prohibited. /Peroxides, Organic and Inorganic/

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Human Toxicity Excerpts · 2 items

ACETYL PEROXIDE IS IRRITATING TO EYES, SKIN, & MUCOUS MEMRANES VIA THE ORAL & INHALATION ROUTES.

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/

Non-Human Toxicity Excerpts · 2 items

Testing on rabbits eyes by application of 2 drops of 30% soln in dimethyl phthalate caused very severe corneal damage.

In most severe injuries induced in rabbits eyes there has been great chemosis and formation of gas bubbles in the conjuctiva, cornea, and anterior chamber. Conjuctiva has become necrotic and cornea opaque. /Org peroxides/

Populations at Special RiskIndividuals with eye, skin, and chronic respiratory diseases /may be/ at an increased risk. /Hydrogen peroxide/
Antidote and Emergency Treatment · 3 items

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. ... Medical attention should also be obtained in case of accidental ingestion. ... /Peroxides, Organic and Inorganic/

Regulatory information

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

Safety data

tsca
TSCA listed
ridadr
3115
hazard_class
5.2
packing_group
II
Hazardous Substances Data
110-22-5(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Absorption, Distribution and ExcretionLIQ ORG PEROXIDES CAN BE ABSORBED THROUGH THE SKIN. /ORG PEROXIDES/

Uses & manufacturing

Uses · 3 items

Used as initiator and catalyst for resins; [Hawley]

Initiator and catalyst for resins

CATALYST EMPLOYED TO PROMOTE POLYMERIZATION IN MFR OF CERTAIN PLASTICS

Formulations/Preparations · 2 items

25% soln in dimethyl phthalate...

...MAY BE READILY PREPD & USED IN ETHEREAL SOLN. ...PREVENT SEPARATION OF THE CRYSTALLINE PEROXIDE EVEN IN TRACE, SINCE, WHEN DRY, IT IS SHOCK-SENSITIVE & HIGH EXPLOSION RISK. ... COMMERCIAL MATERIAL, SUPPLIED AS 30% SOLN IN DIMETHYL PHTHALATE, IS FREE OF TENDENCY TO CRYSTALLIZE & IS RELATIVELY SAFE.

General Manufacturing Information · 2 items

Peroxide, diacetyl: ACTIVE

EMPTY PEROXIDE CONTAINERS SHOULD BE WASHED WITH 10% SODIUM HYDROXIDE SOLN. /25% SOLN/

Applications

UsesDiacetyl peroxide diluted solutions with

General DescriptionColorless liquid with a sharp odor. Consists of a solution of acetyl peroxide in dimethyl phthalate. Sinks in water.

Upstream & downstream products

Downstream products

tert-Butyl cumyl peroxide

Suppliers3 total

陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]

Related reactions

3 records
New reaction record
HRID 1155784 reaction equation
HRID 1155784As reactantuspto-grants-1982_06
HRID 1659443 reaction equation
HRID 1659443As reactantuspto-grants-1981_12
HRID 1703070 reaction equation
HRID 1703070As reactantuspto-grants-1982_09

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes