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Home > Encyclopedia > 3-Methyl-3-buten-2-one

3-Methyl-3-buten-2-one

3-Methyl-3-buten-2-one structure

3-Methyl-3-buten-2-one 

structure
  • CAS No:

    814-78-8

  • Formula:

    C5H8O

  • Chemical Name:

    3-Methyl-3-buten-2-one

  • Synonyms:

    3-Buten-2-one,3-methyl-;3-Methyl-3-buten-2-one;Isopropenyl methyl ketone;2-Methyl-1-buten-3-one;Methyl isopropenyl ketone;3-Methylene-2-butanone;Propen-2-yl methyl ketone;NSC 24150

  • Categories:

    Organic Chemistry  >  Organosulfur Compounds

Description

Colorless or light yellow transparent liquid


Methyl isopropenyl ketone, stabilized appears as a clear colorless liquid. Flash point of 52°F. Denser than water and insoluble in water. Hence sinks in water. Vapors heavier than air.|Liquid


Methyl isopropenyl ketone, stabilized appears as a clear colorless liquid. Flash point of 52°F. Denser than water and insoluble in water. Hence sinks in water. Vapors heavier than air.|3-Methyl-3-buten-2-one is an olefinic compound. It derives from an acrylic acid.

3-Methyl-3-buten-2-one Basic Attributes

84.116

84.12

212-405-1

F64867GQVB

24150

1246

DTXSID9052557

CLEAR, COLORLESS LIQUID

2914190090

Characteristics

17.07000

0.59

Methyl isopropenyl ketone, stabilized appears as a clear colorless liquid. Flash point of 52°F. Denser than water and insoluble in water. Hence sinks in water. Vapors heavier than air.

0.8527 g/cm3 @ Temp: 20 °C

-54 °C

98 °C

11.0±11.9 °C

1.397

SOL IN ALCOHOL

/Store/...at subzero temp to prevent polymerization.

42 MM HG AT 25 DEG C

2.9 (AIR= 1)

(PERCENT PER VOL): LOWER: 1.8; UPPER 9.0

Containers may explode in fire. ... Vapor may explode if ignited in an enclosed area. /inhibited/

PLEASANT

SWEET

CHEMICALLY REACTIVE|Heat of combustion: -15,500 Btu/lb= -8,600 cal/g= -360x10+5 J/kg (est); Heat of vaporization: 182 Btu/lb= 101 cal/g= 4.23x10+5 J/kg (est); surface tension: 26 dynes/cm= 0.026 N/m @ 20 °C (est) /inhibited/

Highly flammable. Insoluble in water.

Ketones

Highly Flammable

METHYL ISOPROPENYL KETONE tends to polymerize; this reaction is mostly suppressed by the inhibitor. Can polymerize if heated or contaminated. If confined in a container when polymerization is initiated, the container may violently rupture (USCG, 1999).

(PERCENT PER VOL): LOWER: 1.8; UPPER 9.0

Safety Information

II

3.1

1246

3

R11

16-29-33-36/37/39

EN0175000

Xi

P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501

H225

Behavior in Fire: May polymerize and explode. (USCG, 1999)|Flammable - 3rd degree, Reactive - 1st degree

|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 126 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 127P [Flammable Liquids (Water-Miscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 127P [Flammable Liquids (Water-Miscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Goggles or face shield; rubber gloves. (USCG, 1999)|PROTECTIVE EQUIPMENT, INCLUDING OCCLUSIVE EYE PROTECTION TO PREVENT EYE DAMAGE BY VAPORS SHOULD BE...USED.|...rubber gloves /inhibited/

Flammable, dangerous fire risk

LOWER = 1.8%, UPPER = 9.0%|Containers may explode in fire. ... Vapor may explode if ignited in an enclosed area. /inhibited/

Dry chemical, foam, carbon dioxide. Water may be ineffective. /inhibited/

A MAXIMUM CONCN OF 0.3 PPM FOR REPEATED EXPOSURES SHOULD BE LOW ENOUGH TO PREVENT LOCAL & SYSTEMIC TOXICITY. ENGINEERING FEATURES...SHOULD INCLUDE GOOD VENTILATION.

/GUIDE 127P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Methyl isopropenyl ketone, inhibited; Methyl isopropenyl ketone, stabilized/|/GUIDE 127P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution. /Methyl isopropenyl ketone, inhibited; Methyl isopropenyl ketone, stabilized/|/GUIDE 127P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Methyl isopropenyl ketone, inhibited; Methyl isopropenyl ketone, stabilized/|/GUIDE 127P: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Methyl isopropenyl ketone, inhibited; Methyl isopropenyl ketone, stabilized/|For more DOT Emergency Guidelines (Complete) data for METHYL ISOPROPENYL KETONE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Vapor: Irritating to eyes, nose & throat; Liquid: Irritating to skin & eyes /inhibited/|...MODERATELY IRRITATING TO SKIN UPON CONTACT. ... ALSO THE VAPORS IN HIGH CONCENTRATION ARE CAPABLE OF CAUSING IRRITATION OF THE SKIN & EVEN A BURN IF EXPOSURE IS PROLONGED. VAPORS ARE ALSO HIGHLY TOXIC AS WELL AS IRRITATING TO THE RESPIRATORY PASSAGES.|...A STRONG LACRIMATOR.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

Short-term exposures...ranging from 0.291 to 14.5 ppm have been reported. There was a questionable odor but no irritation at 0.291 ppm. At 0.77 ppm, there was an immediate definite odor & the vapors were evident to the eyes after a few min. At 1.45 & 2.91 ppm, eye irritation was apparent. At 14.5 ppm, there was an immediate strong odor with eye irritation...after 2 min. Ocular irritation rapidly increased in severity with time. ... Industrial exposures are likely to be by inhalation, skin & eye contact. Its strong irritating & lacrimatory properties may not prevent toxicity because these effects are often not immediately sensed.

Drug Information

Inhalation causes irritation of nose and throat. Liquid may cause severe damage to eyes, resulting possibly in some permanent impairment of vision; vapor produces tears. If not removed promptly from skin, liquid may cause delayed pain and blistering. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

INHALATION: remove victim from exposure; give artificial respiration if needed; call physician. EYES: immediately irrigate with copious amounts of water for 15 min.; call physician. SKIN: wash off skin with large volumes of water for 15 min.; call physician if burn has occurred. INGESTION: induce vomiting; call physician. (USCG, 1999)

...A DEFINITE SKIN IRRITANT. ...DEVELOPMENT OF BLISTERING & PAIN MAY NOT OCCUR IMMEDIATELY UPON CONTACT. SEVERAL MINUTES MAY ELAPSE BEFORE SUCH MANIFESTATIONS ARISE.|...MODERATE TO HIGH DEGREE OF TOXICITY BY SINGLE ORAL EXPOSURE. EYE CONTACT...MAY RESULT IN SEVERE DAMAGE RESULTING...IN...PERMANENT IMPAIRMENT OF VISION... VAPORS ARE ALSO HIGHLY TOXIC AS WELL AS IRRITATING TO THE RESPIRATORY PASSAGES.|METHYL ISOPROPENYL KETONE IS HIGHLY TOXIC BY THE ORAL, PERCUTANEOUS, & RESPIRATORY ROUTES. TOPICAL EXPOSURE TO THE SKIN MAY BE MODERATELY IRRITATING WHILE TOPICAL OR VAPOR EXPOSURE TO THE EYE MAY BE SEVERELY IRRITATING.

3-Methyl-3-buten-2-one Use and Manufacturing

Methods of Manufacturing

...MADE COMMERCIALLY EITHER BY CATALYTIC HYDRATION OF ISOPROPYL ACETYLENE OR BY CONDENSATION OF ACETYLENE WITH ACETONE TO FORM DIMETHYL ETHYNYL CARBINOL, WHICH IS THEN REACTED WITH ACETIC ACID TO FORM DIMETHYL ACETYL CARBINOL ACETATE. THIS IS THEN PYROLYZED TO METHYL ISOPROPENYL KETONE. IT CAN ALSO BE MADE BY REACTING BUTANONE WITH FORMALDEHYDE IN PRESENCE OF CAUSTIC TO YIELD 2-METHYL-3-KETO-BUTANOL, WHICH IS IN TURN CRACKED TO...2-METHYL-1-BUTENE-3-ONE.|CONDENSATION OF METHYL ETHYL KETONE WITH FORMALDEHYDE IN PRESENCE OF NaOH

Uses

Plastics.

Production

(1986) No Data

3-Buten-2-one, 3-methyl-: ACTIVE|Inhibitor of polymerization: up to 1% hydroquinone. /inhibited/

Fire Hazards -> Flammable - 3rd degree, Reactive - 1st degree

Computed Properties

Molecular Weight:84.12
XLogP3:0.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:84.057514874
Monoisotopic Mass:84.057514874
Topological Polar Surface Area:17.1
Heavy Atom Count:6
Complexity:81.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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