Diacetone Alcohol Chemical Properties

Melting point:

-42.8 °C

Boiling point:

166 °C(lit.)

Density 

0.938 g/mL at 20 °C

vapor density 

4 (vs air)

vapor pressure 

<1 mm Hg ( 20 °C)

refractive index 

n20/D 1.423(lit.)

Flash point:

132 °F

storage temp. 

Store below +30°C.

solubility 

Soluble in alcohol, ether (Weast, 1986), and many other solvents, particular ketones such as acetone and 2-butanone.

pka

14.57±0.29(Predicted)

form 

Liquid

color 

Clear colorless

Odor

Mild, pleasant.

explosive limit

1.8-6.9%(V)

Water Solubility 

MISCIBLE

λmax

249nm(lit.)

Merck 

14,2964

BRN 

1740440

Specific Activity

25-50 mCi/mmol

Solvent

Ethanol

Concentration

0.1 mCi/ml

Exposure limits

TLV-TWA 240 mg/m³ (50 ppm) (ACGIH); IDLH 2100 ppm (NIOSH).

Dielectric constant

18.2（Ambient）

Stability:

Stable. Flammable. Incompatible with strong oxidizing agents, amines, ammonia, strong acids, strong bases, alkalies, aluminium.

LogP

-0.09 at 20℃

CAS DataBase Reference

123-42-2(CAS DataBase Reference)

NIST Chemistry Reference

4-Hydroxy-4-methylpentan-2-one(123-42-2)

EPA Substance Registry System

4-Hydroxy-4-methyl-2-pentanone (123-42-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-R36

Safety Statements 

24/25-S24/25

OEB

A

OEL

TWA: 50 ppm (240 mg/m3)

RIDADR 

UN 1148 3/PG 3

WGK Germany 

1

RTECS 

SA9100000

F 

9

Autoignition Temperature

640 °C

TSCA 

Yes

HS Code 

2914 40 10

HazardClass 

3

PackingGroup 

III

Hazardous Substances Data

123-42-2(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 4.0 g/kg (Smyth)

IDLA

1,800 ppm [10% LEL]

MSDS

• Language:English Provider:4-Hydroxy-4-methyl-2-pentanone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Diacetone Alcohol Usage And Synthesis

Application

Diacetone alcohol is available in two grades: a commercial grade containing 15% acetone and an acetone-free grade. Both solvent grades of diacetone alcohol may acquire a yellow color on aging; both are good solvents for nitrocellulose, cellulose esters, and several other types of resins. The much slower evaporating diacetone alcohol is similar to acetone in its solvency. It is used in brushing-type cellulose ester lacquers to produce hard and brilliant gloss films. Diacetone alcohol is also used as lacquer thinner and in coating compositions for paper and textiles. Mesityl oxide, the unsaturated medium boiling point ketone that is prepared by the dehydration of diacetone alcohol, will darken and form a solid residue on aging.

Description

Diacetone alcohol is a colorless liquid with amild, minty odor. Odor threshold = 0.28 ppm. Molecularweight = 116.16; Specific gravity (H2O:1) = 0.94; Boilingpoint = 168℃; Freezing/Melting point = - 43.8℃; Vaporpressure = 1 mmHg at 20℃; Flash point = 64℃; 58℃(acetone free); 64℃ (commercial grade). Explosive limits:LEL = 1.8%; UEL = 6.9%. Hazard Identification (based onNFPA-704 M Rating System): Health 1, Flammability 2,Reactivity 0. Soluble in water.

Chemical Properties

colourless liquid

Chemical Properties

Diacetone alcohol is a colorless liquid. Mild, mint odor.

Physical properties

Clear, watery, flammable liquid with a mild, pleasant, characteristic odor similar to 2-butanone or the pentanones. Experimentally determined detection and recognition odor threshold concentrations were 1.3 mg/m³ (270 ppb_v) and 5.2 mg/m³ (1.1 ppm_v), respectively (Hellman and Small, 1974).

Uses

4-Hydroxy-4-methyl-2-pentanone is used asa solvent for nitrocellulose, cellulose acetate,resins, fats, oils, and waxes; and in hydraulicfluids and antifreeze solutions..

Uses

Solvent for pigments, cellulose, resins, oils, fats, and hydrocarbons; hydraulic brake fluid; antifreeze

Uses

Solvent for cellulose acetate, nitrocellulose, celluloid, fats, oils, waxes, resins. As a preservative in pharmaceutical preparations. In some antifreeze solutions and in hydraulic fluids.

Production Methods

4-Hydroxy-4-methyl-2-pentanone is manufactured through the action of barium hydroxide, potassium hydroxide, or calcium hydroxide on acetone. Commercial materials may contain up to 15%acetone.

Definition

ChEBI: A beta-hydroxy ketone formed by hydroxylation of 4-methylpentan-2-one at the 4-position. It has been isolated from Achnatherum robustum.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 199, 1941
Tetrahedron Letters, 16, p. 4027, 1975 DOI: 10.1016/S0040-4039(00)91227-9

General Description

A clear colorless liquid with a pleasant odor. Flash point below 141°F. Less dense than water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Acetyl bromide reacts violently with alcohols or water, [Merck 11th ed., 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid, [Chem. Eng. News 45(43):73(1967); J, Org. Chem. 28:1893(1963)]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites, [NFPA 491 M, 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Health Hazard

Vapor is irritating to the mucous membrane of the eye and respiratory tract. Inhalation can cause dizziness, nausea, some anesthesia. Very high concentrations have a narcotic effect. The liquid is not highly irritating to the skin but can cause dermatitis.

Health Hazard

4-Hydroxy-4-methyl-2-pentanone is a mildirritant and a strong narcotic. It can causeirritation in the eyes, nose, throat, and skin.The effect on humans, however, is mild at100 ppm concentration.
Animal experiments indicated that it couldproduce sleep after a period of restlessnessand excitement. The symptoms of its toxicity are a marked decrease in breathing andblood pressure, and relaxation of the muscles. Ingestion of this compound in highdoses can damage corneal tissue and liver.The oral toxicity in rats was very low, witha LD50 value of 4000 mg/kg..

Fire Hazard

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. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Chemical Reactivity

Reactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Mddly toxic by skin contact. Human systemic effects by inhalation: headache, nausea or vomiting, eye and pulmonary changes. A skin, mucous membrane, and severe eye irritant. Can cause anemia and damage to liver and hdneys. Narcotic in high concentration. Flammable liquid when exposed to heat or flame; can react with oxidzing materials. Explosive in the form of vapor when exposed to heat or flame. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Potential Exposure

It is used as a solvent for pigments, cellulose esters; oils and fats. It is used in hydraulic brake fluids and in antifreeze formulations.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

Carcinogenicity

Occupational exposure to 4-hydroxy-4-methyl-2- pentanone is most likely to be by inhalation and skin contact. It presents a low degree of hazard if good work practices are observed. Appropriate protective clothing and eye protection should be made available as prolonged exposure may defat the skin and cause dermatitis. The occurrence of eye, nose, and throat irritation and a recognizable odor at low concentrations should protect against overexposure to 4-hydroxy-4- methyl-2-pentanone.

Environmental Fate

Biological. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM diacetone alcohol) and ThOD were 3.67 and 45.9%, respectively (Vaishnav et al., 1987).
Photolytic. Grosjean (1997) reported a rate constant of 4.0 x 10^-12 cm³/molecule?sec at 298 K for the reaction of OH radicals in the atmosphere. Based on a OH concentration of 1.0 x 106 molecule/cm³, the reported half-life of diacetone alcohol is 2.0 d (Grosjean, 1997).

storage

Color Code—Red: Flammability Hazard: Store in aflammable liquid storage area or approved cabinet away fromignition sources and corrosive and reactive materials. Prior toworking with this chemical you should be trained on its properhandling and storage. Before entering confined space wherethis chemical may be present, check to make sure that anexplosive concentration does not exist. Diacetone alcohol mustbe stored to avoid contact with strong oxidizers (such as chlorine, bromine, and fluorine) or strong alkalis (such as sodiumhydroxide or potassium hydroxide) since violent reactionsoccur. Store in tightly closed containers in a cool, wellventilated area away from heat. Sources of ignition, such assmoking and open flames, are prohibited where diacetone alcohol is used, handled, or stored in a manner that could create apotential fire or explosion hazard. Metal containers involvingthe transfer of 5 gallons or more of diacetone alcohol shouldbe grounded and bonded. Drums must be equipped with selfclosing valves, pressure vacuum bungs, and flame arresters.

Shipping

UN1148 Diacetone alcohol, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

The pentanone loses water when heated. It can be dried with CaSO4, then fractionally distilled under reduced pressure. [Beilstein 1 IV 403.]

Incompatibilities

Vapor may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, perox- ides, permanganates, perchlorates, chlorine, bromine, fluo- rine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinera- tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Diacetone Alcohol(123-42-2)Related Product Information

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• 1-Methylcyclopentanol
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• 2,2',4,4'-Tetrahydroxybenzophenone
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