메틸에틸케톤 퍼옥사이드

Methyl ethyl ketone peroxide

HCID 3672772CAS 126-76-1

기본 정보

표준 SMILES
CCC(C)(OO)OOC(C)(CC)OO
InChIKey
WFUGQJXVXHBTEM-UHFFFAOYSA-N
분자식
C8H18O6
평균 분자량
210.22 g/mol
단동위원소 질량
210.11033829

이름 및 식별자

우선 이름
Methyl ethyl ketone peroxide
IUPAC
2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane
현지명
메틸에틸케톤 퍼옥사이드
영어명
2-Butanone peroxide
분자식
C8H18O6
분자량
210.22

이름 및 동의어

2-BUTANONE PEROXIDE1338-23-4Methyl ethyl ketone peroxideThermacureKetonoxMepoxEsperfoam FRLupersol DELButanox LPTQuickset superMEKPQuickset Extra
이름 더 보기
과산화에틸메틸케톤과산화2-부타논메틸에틸케톤퍼옥사이드과산화2-부타논메틸에틸케톤퍼옥사이드2-부탄온 퍼옥사이드과산화 2-부타논메틸 에틸 케톤 과산화물메틸 에틸 케톤 하이드로과산화물에틸 메틸 케톤 과산화물2-부타논과산화물mekpoTrigonox V328fr222permekgpermeknkayameka
2-Butanone, peroxideLucidol delta XMEK peroxideKayamek AKayamek MLupersol DDMLupersol DNFLupersol DSW

데이터베이스 식별자

CAS
126-76-1、1338-23-4
PubChem CID
3672772
DTXSID
DTXSID1024671
ChEMBL
CHEMBL1562553
UNII
W2545087UL
EC Number
215-661-2、700-954-4
Nikkaji
J184.351F

물성

구조 계산 물성

XLogP
1.3
극성 표면적
77.4 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
6
회전 가능 결합 수
7
무거운 원자 수
14

실험 및 물리화학적 성질

Odor · 2건

Typical odor-resembles that of acetone.

Fragrant, mint-like, moderately sharp odor

Density · 4건

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

Relative density (water = 1): 1.10-1.17

1.12

(59 °F): 1.12

Color/Form · 2건

Colorless liquid

Colorless liquid [Note: Explosive decomposition occurs at 230 degrees F].

Solubility · 4건

1 to 5 mg/mL at 72 °F (NTP, 1992)

Partially miscible in water; completely miscible with most organic solvents

Solubility in water: very poor

Soluble

Flash Point · 4건

180 °F (NTP, 1992)

180 °F

125-200 °F for 60% MEKP (open cup)

(oc) 125-200 °F (60% MEKP)

Boiling Point · 5건

244 °F at 760 mmHg (Decomposes) (NIOSH, 2024)

19 °C

244 °F (decomposes)

19 °C @760 [mm Hg]

244 °F (Decomposes)

물리화학적 성질

녹는점
110 °C · 110°C
끓는 점
284 °C · 284 °C
밀도
1.053 g/mL · 1.053 g/mL at 20 °C(lit.)
증기압
0.644 · 0.644-73.6Pa at 25℃
굴절률
20 · n20/D 1.455
인화점
190 °F · 190 °F

화학적 성질

Methyl ethyl ketone peroxide (2-Butanone peroxide) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 7.4% (26 of 349) of reports.

Danger

H242 (90%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides];H302+H332 (29.8%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation];H302 (92.6%): Harmful if swallowed [Warning Acute toxicity, oral];H314 (91.4%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H318 (77.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H332 (30.4%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (29.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P210, P234, P235, P240, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P370+P378, P403, P403+P233, P405, P410, P411, P420, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 349 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 26 of 349 reports by companies.;There are 11 notifications provided by 323 of 349 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

유해성 정보

Regulatory Information · 6건

Chemical: 2-Butanone, peroxide

2-Butanone, peroxide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butanone, peroxide 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: Cease Manufacture Update: 06-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24451

Status: Active Update: 12-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/15761

2-Butanone, peroxide 33-40% in dimethyl phthalate + 1-10% methyl ethyl ketone: HSNO Approval: HSR001376 Approved with controls

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.)

Other Safety InformationIMAP assessments - Selected organic hydroperoxides: Human health tier II assessment
DOT LabelOrganic Peroxide
Fire Hazards · 2건

Behavior in Fire: Explosive. (USCG, 1999)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion on contact with acids, bases or reducing agents.

Health Hazards · 1건

Extremely destructive to tissue of the mucous membranes, upper respiratory tract, eyes, and skin. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

Hazards Summary · 2건

Liquid causes second or third degree burns after short contact. [CHRIS] Corrosive to the eyes, skin, and upper respiratory tract; [ICSC] After ingestion, effects include corrosion and hepatic failure. [HSDB]

The major hazards encountered in the use and handling of 2-butanone peroxide stem from its toxicologic properties and explosivity. Toxic by all routes (ie, inhalation, ingestion, dermal absorption), exposure to this colorless liquid may occur from its production or use as a curing agent for plastics and polyester resins, and as an initiator in the manufacture of polymers. Effects from exposure may include contact burns to the skin and eyes, hemolytic anemia, shortness-of-breath, or pulmonary edema. OSHA has established a Ceiling limit of 0.7 ppm as a final rule to become effective December 31, 1992. In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, irrigate exposed eyes with copious amounts of water for at least 30 minutes, and exposed skin for at least 15 minutes. Contaminated clothing and shoes should be removed at the site. 2-Butanone peroxide may be ignited by heat, sparks, or flames; burning rapidly and producing poisonous gases. Containers of this substance may explode from friction, heat, mechanical shock, or contamination (such as from trace amounts of strong acids, bases, metals, metal alloys, salts, sulfur compounds, amines, accelerators, or reducing agents). For fires involving this substance, extinguish with dry chemical, CO2, regular foam, or water (used in flooding quantities for large fires). Fight fire from as far a distance as possible, in an explosion-resistant location. Isolate the area for 1/2 mile in all directions if a tank, rail car, or tank truck is involved. 2-Butanone peroxide should be stored in cool, ventilated areas, away from sunlight, sources of ignition, physical damage, shock, and organic or flammable materials. Smalls spills of this substance should be taken up with a noncombustible absorbent such as vermiculite and placed in a plastic container for immediate disposal. Wet down large spills with water and dike for lat

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 145 [Organic Peroxides (Heat and Contamination Sensitive)]:;SMALL FIRE: Water spray or fog is preferred; if water not available use dry chemical, CO2 or regular foam.;LARGE FIRE: Flood fire area with water from a distance. Use water spray or fog; avoid aiming straight or solid streams directly onto the product. Do not move cargo or vehicle if cargo has been exposed to heat. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use water spray, powder, carbon dioxide, dry sand, foam. Combat fire from a sheltered position.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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. Do NOT induce vomiting. Refer for medical attention .

First Aid · 2건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Water wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and wash the skin with water. If symptoms occur after washing, get medical attention immediately.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageStore only if stabilized. Well closed. See Chemical Dangers.
Fire Fighting Procedures · 1건

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/

Cleanup Methods · 3건

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/

독성 정보

Interactions · 4건

Vitamin E, selenium, vitamin C, & methionine were admin to rats in various combinations by diet & ip injections to rank the individual & combined protective ability of the biological antioxidants at minimum daily requirement levels & at pharmacological levels against lipid peroxidation initiated by 50 mg methyl ethyl ketone peroxide (MEKP)/kg. In vivo lipid peroxidation was monitored throughout a 3 hr period by measuring pentane expired in the breath. Rats fed 30 IU DL-alpha-tocopherol acetate/mg diet significantly decreased pentane production at 20 min by 88% compared to rats fed a vitamin E- & selenium-deficient diet. Rats given 5 ip injections of 180 IU DL-alpha-tocopherol acetate/kg further reduced expired pentane by 83% beyond the protection afforded by dietary vitamin E. Neither additive nor synergistic protection was found when other antioxidants were given in combination with vitamin E. Vitamin E was primary protective antioxidant. Pentane expired by individual rats from various treatment groups strongly correlated with the plasma vitamin E status.

Male Sprague-Dawley rats were fed 0, 3, 5 or 10 IU of DL-alpha-tocopherol acetate per kg of diet for 12 wk. After 11 weeks they were injected with 3.3 mg of methyl ethyl ketone peroxide (MEKP)/kg body wt & after 12 wk with 13 mg methyl ethyl ketone peroxide/kg body wt 3-4 hr before decapitation. In the absence of vitamin E, rat brain DNA was significantly damaged by the formation of DNA-protein crosslinks & interstrand DNA crosslinks. Adequate dietary vitamin E protected against this damage. 10 IU/kg was the adequate dose.

In vivo, methyl ethyl ketone peroxide damaged microsomal cytochrome p450 and chytochrome p450 mediated peroxidase in vitamin E-deficient rat liver. Dietary vitamin E treatment of rats protected the microsomal enzymes from peroxide damage. In vivo, adequate levels of vitamin E and of NADH and NADPH are probably necessary to provide important protection to the endoplasmic reticulum during metabolism of methyl ethyl ketone peroxide.

The tumor promoting effect of methyl ethyl ketone peroxide and the influence of diethyl maleate on this effect, with ultraviolet radiation as the tumor initiator, was studied in hairless albino mutant mice. Four groups of 24 animals were irradiated with ultraviolet light at a daily dose of 2,054 Joules/sq m, 5 days per week. Three weeks after completion of irradiation, the animals received skin applications twice weekly for 25 weeks of either 1 microgram per microliter diethyl maleate in acetone, acetone alone followed by 0.5 microgram per microliter methyl ethyl ketone peroxide in dibutyl phthalate, or dibutyl phthalate alone. Other groups of animals were treated with chemicals without ultraviolet light pretreatment. The animals were killed after 46 weeks and examined for tumors. The great majority of animals with tumors were in the irradiated groups. The highest tumor yield occurred in mice exposed to both dibutyl phthalate and methyl ethyl ketone peroxide after untraviolet light. Dibutyl maleate alone had no measureable effect on the development of tumors. Methyl ethyl ketone peroxide produced an increase in tumor prevalence, but the effect was less marked than in the combined presence of methyl ethyl ketone peroxide and diethyl maleate.

Target OrgansEyes, skin, respiratory system, liver, kidneys
Health EffectsMEKP is highly irritating and corrosive to skin and mucous membranes. A number of cases in which people accidentally or deliberately ingested MEKP solutions, occasionally with fatal results, have been reported. (L1789)
Environmental Fate · 3건

TERRESTRIAL FATE: 2-Butanone peroxide is a mixture of dimers (50%), and trimers (25%), and monomer peroxy compounds(5). Based on a classification scheme(1), an estimated Koc range of 10 to 11,000(SRC), determined from a structure estimation method(2), indicates that 2-butanone peroxide's mobility in soil is expected to range from very high, to essentially immobile based upon an estimated Koc range of 10 to 11,000(SRC). Volatilization of 2-butanone peroxide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant range of 1X10-10 to 2X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2-Butanone peroxide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure range of 1.4X10-3 to 2X10-3 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: 2-Butanone peroxide is a mixture dimers (50%), trimers (25%), and monomer peroxy compounds(8). Based on a classification scheme(1), an estimated Koc range of 10 to 11,000(SRC), determined from an estimation method(2), indicates that some portions of 2-butanone peroxide mixture are not expected to adsorb to suspended solids and sediment(SRC), other portions of the mixture are expected to adsorb strongly. 2-Butanone peroxide may react with organic materials in water expected(3) based upon estimated Henry's Law constants ranging between 1X10-10 and 2X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 13(SRC), from an estimated log Kow of 2(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: 2-Butanone peroxide is a mixture dimers (50%), trimers (25%), and monomer peroxy compounds(4). According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), the 2-butanone peroxide mixture, which has estimated vapor pressures ranging between 1.4X10-3 and 2X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the vapor-phase in the ambient atmosphere. Vapor-phase 2-butanone peroxide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to range from 1.5 to 2 days(SRC), calculated from its rate constant range of 9X10-12 to 11X10-12 cu cm/molecule-sec at 25 °C(SRC)determined using a structure estimation method(3).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Dermatotoxin - Skin burns.
Exposure Routes · 3건

The substance can be absorbed into the body by inhalation and by ingestion.

inhalation, ingestion, skin and/or eye contact

Oral (L1789) ; inhalation (L1789) ; dermal (L1789)

규제 정보

Regulatory Information · 6건

Chemical: 2-Butanone, peroxide

2-Butanone, peroxide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butanone, peroxide 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: Cease Manufacture Update: 06-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24451

Status: Active Update: 12-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/15761

2-Butanone, peroxide 33-40% in dimethyl phthalate + 1-10% methyl ethyl ketone: HSNO Approval: HSR001376 Approved with controls

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.)

RCRA Requirements · 1건

U160; As stipulated in 40 CFR 261.33, when 2-butanone peroxide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

안전 데이터

OEL
Ceiling: 0.2 ppm (1.5 mg/m3)
wgk
1
tsca
TSCA listed
ridadr
UN 3105 5.2
risk_code
8-22-38-41-43-34-7-35-23-9-62-50/53-61
hazard_code
O,Xn,C,T,N

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

The stability of glutathione peroxidase was assessed in vivo via oxidative inactivation by methyl ethyl ketone peroxide. The stability of glutathione peroxidase was compared to other enzymes. Some of the enzymes tested were very stable to methyl ethyl ketone peroxide. Glutathione peroxidase in the absence of glutathione was relatively slowly inactivated. Thus, glutathione peroxidase appears to be a relatively stable enzyme & is well suited to perform its role in peroxide detoxification & prevention of oxidative deterioration of cells.

용도 및 제조

Uses · 6건

Used as a curing agent in the production of plastics, adhesives, lacquers, and fiberglass; [HSDB]

Painting (Pigments, Binders, and Biocides) [Category: Paint];Working with Glues and Adhesives [Category: Other];Plastic Composites Manufacturing [Category: Industry]

Sculpturing plastics [Category: Hobbies]

Manufacture of acrylic resins; hardening agent for fiberglass-reinforced plastics.

MEDICATION

Unsaturated polyester resin crosslinking agent

U.S. Imports(1977) AT LEAST 4.54X10+5 G
U.S. Production · 6건

2023: 10,000,000 - <50,000,000 lb;2022: 10,000,000 - <50,000,000 lb;2021: 10,000,000 - <50,000,000 lb;2020: 10,000,000 - <50,000,000 lb

(1978) 4.09X10+8 G

(1982) 2.68X10+9 G

(1985) 4.43X10+8 g.

(1992) 4,520,000 kg

(1993) 5,107,000 kg

Consumption PatternsCURING AGENT FOR UNSATURATED POLYESTER RESINS, 94%; OTHER USES, 6% (1980).
Consumer UsesHardener
Industry UsesCBI;Polymerization promoter

응용 분야

일반 설명Colorless liquid. Strong irritant to skin and tissue. Used as an initiator for room temperature cure of unsaturated polyester resins.

제조 방법 · 1건

2-Butanone peroxide is obtained by reacting methyl ethyl ketone with hydrogen peroxide (hydrogen peroxide) in the presence of sulfuric acid. After oxidation, neutralization, separation, dehydration, standing, filtration, and finally adding the solubilizing agent to obtain the finished product.

공급사50 곳

Hebei Jingbo New Material Technology Co., Ltd+86-19931165850 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]
武汉欣扬瑞和化学科技有限公司18171205315; 18171205315 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]

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