Diacetone Alcohol

HCID 31256CAS 123-42-2

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

Diacetone alcohol4-HYDROXY-4-METHYL-2-PENTANONE123-42-24-Hydroxy-4-methylpentan-2-oneDiacetonalkoholDiketone alcoholDiacetonalcoholTyrantonAcetonyldimethylcarbinolPyranton ADiacetonePyranton
Weitere Namen anzeigen
DAADiacetone alcoho2-Hydroxy-2-methyl-4-pentanone
Diacetone-alcool2-Pentanone, 4-hydroxy-4-methyl-Diacetonalcool2-Methyl-2-pentanol-4-oneDiacetonyl alcohol4-Hydroxy-2-keto-4-methylpentane4-Idrossi-4-metil-pentan-2-oneDimethyl acetonyl carbinol

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SolventsSolvents -> Other Solvents
Cosmetics · 2 Einträge

Cosmetic ingredients (Diacetone Alcohol) -> CIR (Cosmetic Ingredient Review)

Solvent

SpringerMaterials PropertiesBoiling point
LogP-0.14 - 1.03 (calculated)

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.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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 · 6 Einträge

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.)

Other Safety InformationIMAP assessments - 2-Pentanone, 4-hydroxy-4-methyl-: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

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.

Fire PotentialMODERATE WHEN EXPOSED TO HEAT OR FLAME ...
Health Hazards · 2 Einträge

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.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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 · 4 Einträge

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 · 2 Einträge

· 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 · 3 Einträge

Excerpt from NIOSH Pocket Guide for Diacetone alcohol:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from acids, bases, amines and oxidants.
Firefighting HazardsFlashback along vapor trail may occur.

Toxikologische Informationen

Target OrgansEyes, skin, respiratory system, central nervous system, liver
Ecotoxicity Values · 3 Einträge

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 · 3 Einträge

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 · 1 Eintrag

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).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 Einträge

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

Regulatorische Informationen

FDA RequirementsDiacetone alcohol is an indirect food additive for use only as a component of adhesives.
FIFRA Requirements · 1 Eintrag

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 · 1 Eintrag

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

Chemie und Industrie

Pharmakologische Informationen

Absorption, Distribution and Excretion · 2 Einträge

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.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 6 Einträge

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

ImpuritiesTECHNICAL GRADE CONTAINS UP TO 15% ACETONE.
U.S. Production · 3 Einträge

2023: 10,000,000 - <25,000,000 lb

(1972) 4.83X10+10 GRAMS

(1975) 1.79X10+10 GRAMS (SALES)

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesCleaning agent
Methods of Manufacturing... ACTION OF BARIUM HYDROXIDE OR ... CALCIUM HYDROXIDE ON ACETONE. INDUSTRIAL PROCESS USING POTASSIUM HYDROXIDE & ACETONE.
Anwendungen · 2 Einträge

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.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]

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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