Grundinformationen
- Standard-SMILES
CC(=O)CC(C)(C)O- InChIKey
SWXVUIWOUIDPGS-UHFFFAOYSA-N- Summenformel
- C6H12O2
- Durchschnittliche Molmasse
- 116,16 g/mol
- Monoisotopische Masse
- 116,08372962
Überblick
Diacetone alcohol appears as a clear colorless liquid with a pleasant odor. Flash point below 141 °F. Less dense than water. Vapors heavier than air.
Namen und Bezeichner
- Bevorzugter Name
- Diacetone Alcohol
- IUPAC
- 4-hydroxy-4-methylpentan-2-one
- Lokaler Name
- 4-Hydroxy-4-methylpentan-2-on
- Englischer Name
- Diacetone Alcohol
- Summenformel
- C6H12O2
- Molmasse
- 116.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
123-42-2- PubChem CID
- 31256
- DTXSID
DTXSID6024917- ChEMBL
CHEMBL3182048- ChEBI
CHEBI:55381- UNII
- Q7WP157PTD
- EC Number
- 204-626-7
- Nikkaji
- J5.540I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,2
- Polarare Oberfläche (TPSA)
- 37,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 94,7
Experimentelle und physikochemische Eigenschaften
Cosmetics
Cosmetic ingredients (Diacetone Alcohol) -> CIR (Cosmetic Ingredient Review)
Solvent
Odor
FAINT PLEASANT ODOR
Minty odor
Density
0.938 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9306 @ 25 °C/4 °C (0.940 FOR TECHNICAL GRADE)
PERCENT IN SATURATED AIR: 0.13 (20 °C); DENSITY OF SATURATED AIR: 1.005 (AIR= 1)
Relative density (water = 1): 0.93
0.94
0.9306 @ 20°C
Color/Form
COLORLESS LIQUID
Colorless liquid.
Faint, minty odor.
Solubility
Miscible (NIOSH, 2024)
MISCIBLE WITH WATER, ALCOHOL, ETHER, OTHER SOLVENTS
Water solubility of 1.0X10+6 mg/l
1000 mg/mL at 25 °C
Solubility in water: miscible
Miscible
Flash Point
125 °F (USCG, 1999)
66 °C
66 °C (OPEN CUP); COMMERCIAL GRADE IS 8 °C (CLOSED CUP) & 13 °C (OPEN CUP)
58 °C c.c.
125 °F
125 °F
Physikochemische Eigenschaften
- Schmelzpunkt
- -42.8 °C · -42.8 °C
- Siedepunkt
- 166 °C · 166 °C(lit.)
- Dichte
- 0.938 g/mL · 0.938 g/mL at 20 °C
- Dampfdichte
- 4 · 4 (vs air)
- Dampfdruck
- 1 mm · <1 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.423(lit.)
- Flammpunkt
- 132 °F · 132 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- Soluble in alcohol, ether (Weast, 1986), and many other solvents, particular ketones such as acetone and 2-butanone.
- pka
- 14.57 · 14.57±0.29(Predicted)
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless
- Geruch (Odor)
- Mild, pleasant.
- Explosionsgrenze
- 1.8 · 1.8-6.9%(V)
- Wasserlöslichkeit
- MISCIBLE
- Spezifische Wärmekapazität
- 1.91 J/ · Cp(liquid): 1.91 J/(g·K), at 25℃
- Merck
- 14 · 14,2964
- BRN
- 1740440 · 1740440
- Specific Activity
- 25 · 25-50 mCi/mmol
- Henry's Law Constant
- 3.8 · 3.8×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 18.2 · 18.2(Ambient)
- Stabilität
- Stable. Flammable. Incompatible with strong oxidizing agents, amines, ammonia, strong acids, strong bases, alkalies, aluminium.
- Kosmetik-Inhaltsstoffe Funktionen
- PERFUMINGSOLVENTFRAGRANCE
- InChI
- 1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
- InChIKey
- SWXVUIWOUIDPGS-UHFFFAOYSA-N
- SMILES
- CC(=O)CC(C)(C)O
- LogP
- -0.09 at · -0.09 at 20℃
- Oberflächenspannung
- 29.44 mN/m · 29.44 mN/m at 303.15K
- CAS Datenbank
- 123 · 123-42-2(CAS DataBase Reference)
- NIST chemische Informationen
- 4 · 4-Hydroxy-4-methylpentan-2-one(123-42-2)
- EPA chemische Informationen
- 4 · 4-Hydroxy-4-methyl-2-pentanone (123-42-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1556) of reports.
Warning
H226 (32.3%): Flammable liquid and vapor [Warning Flammable liquids]
Gefahrenhinweise
Regulatory Information
Chemical: 2-Pentanone, 4-hydroxy-4-methyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
2-Pentanone, 4-hydroxy-4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Pentanone, 4-hydroxy-4-methyl- 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: 21-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13357
2-Pentanone, 4-hydroxy-4-methyl-: HSNO Approval: HSR001120 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.)
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Flammable. Above 58 °C explosive vapour/air mixtures may be formed.
Health Hazards
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. (USCG, 1999)
· May cause toxic effects if inhaled or absorbed through skin.
DOT ID and Guide
1148 129
1148 129
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Use water spray, alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
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. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from NIOSH Pocket Guide for Diacetone alcohol:
General First Aid:
(General first aid procedures)
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
20.0 [ppm]
Fire Fighting Procedures
ALCOHOL FOAM, FOAM, CARBON DIOXIDE, DRY CHEMICAL ... .
Wear goggles & self contained breathing apparatus. Water may be ineffective.
Storage Conditions
... MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL WELL-VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED ... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED ... .
Preventive Measures
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
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.
Toxikologische Informationen
Ecotoxicity Values
LC50 Lepomis macrochirus 420 ppm/96 hr (static bioassay in fresh water at 23 °C, mild aeration applied after 24 hr).
LC50 Menidia beryllina 420 ppm/96 hr (static bioassay in synthetic sea water at 23 °C, mild aeration applied after 24 hr).
LD50 Goldfish > 5000 mg/l/24 hr. /Conditions of bioassay not specified/
Environmental Fate
TERRESTRIAL FATE: If 4-hydroxy-4-methyl-2-pentanone is released to soil, it will be expected to exhibit very high mobility(1), based upon the reported infinite solubility of the compound in water(2) and an estimated Koc of 21 calculated(3,SRC) from a measured log Kow(4). The compound may, therefore, leach through soil to groundwater if it does not biodegrade first(SRC). It may be subject to biodegradation in soil based upon results observed in laboratory biodegradation aqueous aerobic screening tests using acclimated mixed microbial cultures as inoculums(5,6) provided suitably acclimated microbial populations are present(7,SRC). It should not be subject to volatilization from moist near surface soil based upon(3,SRC) an estimated Henry's Law constant of 4.24X10-9 atm-cu m/mole(9,SRC). However, it may volatilize from dry near-surface soil and other dry surfaces based upon its vapor pressure of 1.71 mm Hg at 25 °C(8).
AQUATIC FATE: If 4-hydroxy-4-methyl-2-pentanone is released to water, it will not be expected to adsorb to sediment or suspended particulate matter or to bioconcentrate in aquatic organisms based upon its estimated Koc and BCF, respectively, calculated(1,SRC) from the measured log Kow(2), and its high solubility in water(3). Although no data were found regarding biodegradation in environmental media, the compound may be subject to biodegradation in natural waters based upon results observed in laboratory aqueous aerobic biodegradation screening tests using acclimated mixed microbial cultures as inoculums(4,5) provided suitably acclimated microbial populations are present(6,SRC). It should not be subject to volatilization from surface waters based upon(1,SRC) an estimated Henry's Law constant of 4.24X10-9 atm-cu m/mole(7,SRC) Hydrolysis should not be an important removal process since aliphatic alcohols and ketones (the two functional groups that 4-hydroxy-4-methyl-2-pentanone contains) generally are resistant to hydrolysis(1).
ATMOSPHERIC FATE: If 4-hydroxy-4-methyl-2-pentanone is released to the atmosphere, it can be expected to exist mainly in the vapor-phase in the ambient atmosphere(1,SRC) based upon an experimental vapor pressure of 1.71 mm Hg at 25 °C(2). The estimated rate constant for vapor-phase reaction with photochemically produced hydroxyl radicals is 1.34X10-12 cu cm/molecule-sec at 25 °C(3) which corresponds to an atmospheric half-life of 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). 4-Hydroxy-4-methyl-2-pentanone may be susceptible to direct photolysis in the atmosphere(SRC) based upon its possible absorption(SRC) of light at wavelengths >290 nm(4). Based upon its high water solubility(5), the compound may be susceptible to removal from the atmosphere by washout(SRC).
Food Survey Values
4-Hydroxy-4-methyl-2-pentanone has been qualitatively detected in foodstuffs exposed to acetone: meat carcasses exposed to surfaces that were freshly painted with acetone containing paints and vegetables and seeds which were extracted with acetone(1).
Exposure Routes
The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
inhalation, ingestion, skin and/or eye contact
Signs and Symptoms
Cough. Sore throat.
Redness. Dry skin. MAY BE ABSORBED!
Redness. Pain.
irritation eyes, skin, nose, throat; corneal damage; In Animals: narcosis, liver damage
Effluent Concentrations
4-Hydroxy-4-methyl-2-pentanone was qualitatively detected in 2 out of >4000 samples of effluent from 2 of 46 industrial categories (organics and plastics manufacture and rubber processing)(1). It was qualitatively detected in 4 of 16 samples of concentrate derived from large volume (>400 gallons) samples of advanced treatment concentrate from 4 of 6 cities (Lake Tahoe, CA, Oct 1974; Pomona, CA, Sept 1974; Orange County, CA, Feb 1976; and Blue Plains, Washington, DC, May 1975)(2). The compound was detected in samples of water from landfill monitoring well in New Castle, DE at concn of 2,900 ppm(3). It was qualitatively detected in a petrochemical plant wastewater stream which emptied into the Calcasieu River, LA(4). The compound was detected at an estimated concn of 10.9 ppb in groundwater from a landfill well near Norman, OK (concn was estimated by comparing gas chromatography peak heights of samples with that obtained for know concn of the compound)(5).
It was detected at a concn of 20 ppb in the effluent for the Los Angeles County wastewater treatment plant between Nov 1980 and Aug 1981(1). The compound was qualitatively detected in the final effluent from the Addison, IL publicly-owned treatment works sampled in April 1980; it was not detected (detection limit not specified) in the final effluent from seven other publicly-owned treatment works, a refinery and an industrial plant in Illinois sampled between Feb and June 1980(2). It was qualitatively found in trench leachate from low level radioactive waste sites at Maxey Flats, KY and/or West Valley, NY(3). The compound was found in spent chlorination liquor from bleaching of sulfite pulp at normal lignin content after oxygen treatment at a concn of 1 g/ton of pulp, at 9 g/ton pulp in spent chlorination liquor from bleaching of sulfite pulp at normal lignin content after oxygen and alkali treatments and at 0.3 g/ton in spent chlorination liquor from bleaching of sulfite pulp at high lignin content(4).
Soil Adsorption/Mobility
An estimated Koc of 21 can be calculated(SRC) from an estimated log Kow of -0.098(2) using a recommended regression equation(1). Based upon the estimated Koc and the reported infinite solubility of the compound in water(3), 4-hydroxy-4-methyl-2-pentanone will not be expected to strongly adsorb to sediment or suspended particulate matter(4,SRC). It will be expected to exhibit very high mobility in soil(4), and therefore, 4-hydroxy-4-methyl-2-pentanone may leach through soil to groundwater if it does not volatilize or biodegrade first(SRC).
Human Toxicity Excerpts
... High concn of vapor produce ... /CNS depression/ & systemic injury. ...
A 59 year old man developed a nephrotic syndrome 40 days after hydrocarbon (diacetone alcohol & ethanol point solvents) exposure of 3 day duration. Renal biopsy gave evidence of a subacute proliferative glomerulonephritis. A lasting remission was obtained with immunosuppressive therapy.
... Prolonged contact may defat skin & cause dermatitis. ... Death may result from resp failure due to depression of resp center. Additional effects are renal & hepatic injury & decr blood pressure.
If spilled on clothing & allowed to remain, may cause smarting & reddening of skin.
/Diacetone alcohol/ ... at higher concentrations ... causes excitement and sleepiness. Prolonged exposure may result in liver and kidney damage and in blood changes.
Regulatorische Informationen
FIFRA Requirements
Diacetone alcohol is exempted from the requirement of a tolerance when used as a deactivator or a solvent for formulations used before crop emerges from the soil in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diacetone alcohol is produced, as an intermediate or final product, by process units covered under this subpart.
Sicherheitsdaten
- F
- 9
- OEB
- A
- OEL
- TWA: 50 ppm (240 mg/m3)
- wgk
- 1
- IDLA
- 1,800 ppm [10% LEL]
- tsca
- TSCA listed
- ridadr
- UN 1148 3/PG II/III (DIACETONE ALCOHOL)
- hs_code
- 2914 40 10
- RTECS-Nr.
- SA9100000
- risk_code
- 36-R36
- Toxizität
- LD50 orally in rats: 4.0 g/kg (Smyth)
- hazard_code
- Xi
- safety_code
- 24/25-S24/25
- hazard_class
- 3
- packing_group
- III
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 123-42-2(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 3Repr. 2STOT SE 3
- Selbstentzündungstemperatur
- 640 °C
Chemie und Industrie
Pharmakologische Informationen
Absorption, Distribution and Excretion
ABSORPTION ... OCCURS READILY FROM THE LUNG.
Distribution of label during anesthesia of rats with labeled diacetone alcohol was mainly in extracellular fluid rather than in erythrocytes or brain cells.
Verwendung und Herstellung
Uses
CIR ingredient: Diacetone Alcohol
Used in antifreeze and brake fluids; also used as a solvent to make nitrocellulose, cellulose acetate, celluloid, pigments, waxes, and oils; [ACGIH]
Painting (Solvents) [Category: Paint]
INT IN SYNTH OF MESITYL OXIDE, HEXALENE GLYCOL AND OTHER ORG CHEMS
SOLVENT FOR CELLULOSE ACETATE, NITROCELLULOSE, CELLULOID, FATS, OILS, WAXES, RESINS; IN SOME ANTIFREEZE SOLUTIONS & HYDRAULIC FLUIDS; PRESERVATIVE IN PHARMACEUTICAL PREPN
COATING COMPOSITIONS & MERCERIZATIONS; SOLVENT FOR CERTAIN PIGMENTS; MANUFACTURE OF QUICK DRYING INKS, PHOTOGRAPHIC FILM, METAL CLEANING CMPD
U.S. Production
2023: 10,000,000 - <25,000,000 lb
(1972) 4.83X10+10 GRAMS
(1975) 1.79X10+10 GRAMS (SALES)
General Manufacturing Information
Synthetic Dye and Pigment Manufacturing
2-Pentanone, 4-hydroxy-4-methyl-: ACTIVE
Anwendungen
BeschreibungDiacetonalkohol ist eine farblose, fast geruchsfreie Flüssigkeit mit einem Siedepunkt von 168 ℃ bei bei 760 Torr. Es ist eine Zwischenstufe bei der Synthese von Mesityloxid, Methylisobutylketon und Hexylenglykol. Außerdem ist es ein gutes Lösungsmittel für viele Cellulose-Verbindungen sowie Natur- und Kunstharze.
VerwendenSolvent for cellulose acetate, nitrocellulose, celluloid, fats, oils, waxes, resins. As a preservative in pharmaceutical preparations. In some antifreeze solutions and in hydraulic fluids.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A beta-hydroxy ketone formed by hydroxylation of 4-methylpentan-2-one at the 4-position. It has been isolated from Achnatherum robustum.
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