アセチルアセトン

Acetylacetone

HCID 31261

基本情報

CAS
123-54-6
標準SMILES
CC(=O)CC(C)=O
InChIKey
YRKCREAYFQTBPV-UHFFFAOYSA-N
分子式
C5H8O2
平均分子量
100.12 g/mol
単同位体質量
100.05242949

名称と識別子

優先名称
Acetylacetone
IUPAC
pentane-2,4-dione
現地名
アセチルアセトン
英語名
Acetylacetone
分子式
C5H8O2
分子量
100.12

名称と別名

2,4-PentanedioneAcetylacetonePentane-2,4-dione123-54-62,4-DioxopentaneAcetoacetoneDiacetylmethaneACACPentanedioneACETYL ACETONEPentan-2,4-dionePentanedione-2,4
名称をさらに表示
アセチルアセトン2,4-ペンタジオンペンタン-2,4-ジオン2,4-ペンタンジオンメチル(2-オキソプロピル)ケトンジアセトン2,4-ジオキソペンタンジアセチルメタン2,4ペンタンジオン2,4-ペンタンジオン(アセチルアセトン)アセチルアセトン (別名: 2,4-ペンタンジオン)アセチルアセトン 2,4-ペンタンジオンアセチルアセトン PURISS. P.A.,≥99.5% (GC)アセチルアセトン REAGENTPLUS,≥99%アセチルアセトン2,4-ペンタンジオンアセチルアセトン(AA)2 , 4 - ペンタンジオン(アセチルアセトン)AAacetylACETYLPROPIONYL2,4-PENTADIONEFEMA 2841
Acetyl 2-propanoneAcetone, acetyl-Hacac2-Propanone, acetyl-DTXSID402197946R950BP4JNSC-5575DTXCID601979

データベース識別子

CAS
123-54-6
PubChem CID
31261
DTXSID
DTXSID4021979
ChEMBL
CHEMBL191625
ChEBI
CHEBI:14750
UNII
46R950BP4J
EC Number
204-634-0
Nikkaji
J2.499F

物性

構造計算による物性

XLogP
0.4
極性表面積
34.1 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
2
重原子数
7

実験および物理化学的性質

LogP · 2 件

log Kow = 0.40

0.40

Odor · 2 件

Pleasant odor

Mild ketone-like odor

Density · 6 件

0.975 at 68 °F (USCG, 1999) - Less dense than water; will float

0.9721 at 25 °C/4 °C

Bulk density = 8.1 lb/gal

Relative density (water = 1): 0.98

0.975

0.9721 @25 °C

Viscosity0.6 mPa.s at 20 °C
Color/Form · 2 件

Colorless or slightly yellow liquid

Mobile, colorless or yellowish liquid; when cooled, solidifies to lustrous, pearly spangles. The liquid is affected by light, turning brown and forming resins.

Solubility · 6 件

In water, 166,000 mg/L at 20 °C

One part dissolves in about 8 parts water

Fairly soluble in neutral water

Miscible with alcohol, ether, chloroform, benzene, acetone, glacial acetic acid

For more Solubility (Complete) data for Acetyl acetone (7 total), please visit the HSDB record page.

166 mg/mL at 20 °C

物理化学的性質

融点
-23 °C · -23 °C (lit.)
沸点
140.4 °C · 140.4 °C (lit.)
比重(密度)
0.975 g/mL · 0.975 g/mL at 25 °C (lit.)
蒸気密度
3.5 · 3.5 (vs air)
蒸気圧
6 mm · 6 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.452(lit.)
化学的性質 · 2 件

化学的特性Acetylacetone is a β-diketone derived from pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups. It is the conjugate acid of acetylacetonate.Acetylacetone is a colorless to yellowish liquid with a sour, rancid odor. Its odor threshold is 0.01 ppm. It has an ethereal, minty odor with somewhat metallic or chemical notes. At high dilution in an aqueous medium, it has a sweet flavor remotely reminiscent of peppermint.Acetylacetone is not very stable and readily exists as an equilibrium mixture of its keto and enol forms. It can be produced from acetone and ethyl acetate or from acetone and acetic anhydride in the presence of boron trifluoride.

化学性质エチレンプロピレンは広く使われている合成ゴムの一種ですこの材料はエチレンとプロピレンという二つの単純な炭化水素化合物から成り立っています耐候性耐熱性そして耐寒性に優れているため自動車産業や建築業界など多岐にわたる分野で使用されています

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids];H302: Harmful if swallowed [Warning Acute toxicity, oral]

P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P317, P303+P361+P353, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Danger

危険有害性情報

Regulatory Information · 6 件

Chemical: 2,4-Pentanedione

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2,4-Pentanedione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Pentanedione 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)

SP - indicates a substance that is identified in a proposed Significant New Use Rule.

Status: Active Update: 30-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14713;Status: Active Update: 10-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33689

2,4-Pentanedione: HSNO Approval: HSR001072 Approved with controls

Other Safety InformationIMAP assessments - 2,4-Pentanedione: Human health tier II assessment
DOT LabelFlammable Liquid Poison
Fire Hazards · 3 件

Behavior in Fire: Vapor is heavier than air and may travel to a source of ignition and flash back. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;CAUTION: Methanol (UN1230) will burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.);· 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 the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion and poison 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 will float on water.

Flammable. Above 34 °C explosive vapour/air mixtures may be formed.

Fire Potential · 2 件

Flammable liquid when exposed to heat or flame.

Moderate fire risk.

Health Hazards · 2 件

Inhalation causes dizziness, headache, nausea, vomiting and loss of consciousness. Contact with liquid irritates eyes. (USCG, 1999)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.;· Inhalation or contact with some of these materials will irritate or burn skin and eyes.;· Methyl chloroacetate (UN2295) is an eye irritant/lachrymator (causes flow of tears).;· Fire will produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: Methanol (UN1230) will burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.).;SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam.;LARGE FIRE: Water spray, fog or alcohol-resistant foam. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal. Avoid aiming straight or solid streams directly onto the product.;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. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. 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 powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

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. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

Accidental Release Measures · 2 件

· 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.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from 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.;Small Spill;· Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal.;· 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.

First Aid · 2 件

INHALATION: remove to fresh air; if victim is not breathing, give artificial respiration and then oxygen; call a physician.;EYES or SKIN: flush with water. (USCG, 1999)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.

Safe StorageFireproof. Separated from strong oxidants. Keep in the dark.
Firefighting Hazards · 1 件

Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions.

毒性情報

Interactions · 2 件

When 2,4-pentanedione was incubated with yeast cells, no chromosome loss occurred even at a concentration of 1.96% (v/v) and cold shock, but the addition of propionitrile to the incubation mixture stimulated chromosomal loss.

... Acetylacetone inhibited the mutagenicity of 2-naphthohydroxamic acid.

Ecotoxicity Values · 5 件

LC50; Species: Pimephales promelas (fathead minnow); Concentration: 200 mg/L for 24 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through, Lake Superior water, 25.2 °C, 6.3 dissolved oxygen, Hardness 46.5 mg/L CaCO3, pH 7.37; Concentration: 104 mg/L for 96 hr (95% confidence interval: 98.3-110 mg/L)... /Purity >99%/

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through, temperature 18.6 to 19.4 °C, pH 7.65 to 7.94, dissolved oxygen (DO) 6.19 to 9.22 mg/L, hardness (CaCO3) 196 mg/L; Concentration: 141 mg/L for 96 hr /Purity > 99%/

LC50; Species: Pimephales promelas (fathead minnow) 28 to 34 days-old; Conditions: flow-through with 99% replacement in about 2 hr; dissolved oxygen 7.57 mg/L, pH 7.32, 43.2 mg/L CaCO3, temperature 24 to 26 °C; Concentration: 142 mg/L for 96 hr /Purity >99%/

For more Ecotoxicity Values (Complete) data for Acetyl acetone (72 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.40(2) and a regression-derived equation(3), indicates that acetyl acetone is expected to have very high mobility in soil(SRC). Volatilization of acetyl acetone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2.96 mm Hg(4), and water solubility, 166,000 mg/L(5). Acetyl acetone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Utilizing the Japanese MITI test, 83% of the Theoretical BOD was reached in 4 weeks(6), suggesting that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.40(2) and a regression-derived equation(3), indicates that acetyl acetone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.96 mm Hg(5), and water solubility, 166,000 mg/L(6). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 16 days and 120 days, respectively(SRC). The aquatic oxidation rate for acetyl acetone has been experimentally determined to be 9.9X10-9 L/mol-s at pH 6.4(7). Based on this rate and a hydroxyl radical concentration of 1X10-17 mol/L in water under continuous sunlight(8), the half-life for the aquatic oxidation of acetyl acetone can be estimated to be 81 days(SRC). According to a classification scheme(9), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 83% of the Theoretical BOD was reached in 4 weeks(10), suggesting that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetyl acetone, which has a vapor pressure of 2.96 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetyl acetone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 22 days(SRC), calculated from its rate constant of 9.05X10-11 cu cm/molecule-sec at 25 °C(3). Acetyl acetone absorbs UV light at wavelengths >314 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesAcetyl acetone has been identified, not quantified in chicken(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

法規制情報

Regulatory Information · 6 件

Chemical: 2,4-Pentanedione

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2,4-Pentanedione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,4-Pentanedione 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)

SP - indicates a substance that is identified in a proposed Significant New Use Rule.

Status: Active Update: 30-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14713;Status: Active Update: 10-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33689

2,4-Pentanedione: HSNO Approval: HSR001072 Approved with controls

FDA Requirements2,4-Pentanedione is an indirect food additive for use only as a component of adhesives.
TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2,4-Pentanedione is included on this list. Effective date: 9/30/91; Sunset date: 12/19/95.

安全データ

F
9-23
wgk
1
tsca
TSCA listed
rtecs
SA1925000
ridadr
UN 2310 (PENTANE-2,4-DIONE)
毒性
LC50 (4 hrs) in rats: 1000 ppm (Carpenter)

化学と産業

薬理情報

Biological Half-LifeAbout 10.75 hours in rats; [ACGIH]
Absorption, Distribution and Excretion · 1 件

2,4-Pentanedione (2,4-PD; CAS No. 123-54-6) ... was investigated for its comparative pharmacokinetics in male Fischer 344 rats by a single intravenous (i.v.) injection of (4.3, 43, 148.5, and 430 mg/kg), or a 6-hr nose-only inhalation exposure (400 ppm) to (14)C-2,4-PD. For the i.v. route, the plasma concentration of (14)C-2,4-PD-derived radioactivity declined in a biexponential fashion. The overall form of the (14)C plasma concentration-time curves and derived pharmacokinetic parameters indicated that dose-linear kinetics occurred in the i.v. dose range 4.3-148.5 mg/kg, but not with 430 mg/kg. Metabolism of 2,4-PD was rapid to undetectable after 8 hr. (14)C-2,4-PD derived radioactivity was eliminated mainly as (14)CO2 and in urine. For the 4.3, 43 and 148.5 mg/kg doses (14)CO2 elimination was relatively constant (36.8, 38.8 and 42.3% in 48 hr samples respectively) and greater than urinary excretion (17.9, 14.3 and 29.6%; 48 hr specimens). At 430 mg/kg i.v. there was a reversal of the excretion pattern, with urine (14)C excretion (54.7%) becoming greater than that for (14)CO2 (27.3%). Excretion in expired volatiles and feces was small. Radiochromatograms of urine showed free 2,4-PD in the 12 hr sample, together with 7 other metabolites. Free 2,4-PD and 6 of the metabolites decreased or were not detectable in a 24 or 48 hr urine sample, but one peak (retention 7.9 min) increased progressively to become the major fraction (97%). Nose-only exposure to 400 ppm (14)C-2, 4-PD produced a mean decrease in breathing rate of 20.1%, which was constant and sustained throughout exposure, due to a lengthening of the expiratory phase of the respiratory cycle. (14)C-2,4-PD was rapidly absorbed during the first 3 hr of exposure, then began to plateau, but did not reach a steady state. Postexposure elimination of (14)C from plasma followed a biexponential form with a t1/2 for the terminal disposition phase of 30.72 hr. ... Postexposure, plasma unmetabolized 2,4-PD declined rapidly to

Cellular LocationsCytoplasm;Extracellular

用途と製造

Uses · 6 件

Used as a chemical intermediate, solvent, metal chelating agent, lubricant additive, and pesticide; [Hawley] Used as a metal chelator, lubricant additive, corrosion inhibitor, polyolefin modifier, and intermediate; [ACGIH]

Painting (Solvents) [Category: Paint]

Forms organometallic complexes which are used as gasoline additives, lubricant additives, driers for varnishes and printer's inks ... .

Fungicides, insecticides, colors /SRP: Former uses/

Solvent for cellulose acetate, intermediate, chelating agent for metals, paint driers, lubricant additives.

2,4-Pentanedione is used as an intermediate, in particular for the synthesis of heterocyclic substances for biologically active compounds and dyes, and for the production of metal acetylacetonates. Furthermore, 2,4-pentanedione is used as a solvent, and as an absorption and extraction agent, particularly for the separation and purification of metal ions. Another application is for the purification of metal-containing wastewater and for corrosion protection. 2,4-Pentanedione is also used as a component of catalyst systems for polymerization, copolymerization, oligo- and dimerization.

ImpuritiesThe purity of the substance exceeds 99%. Known impurities are water (0.1%), hexane-2,5-dione (0.1%), acetic acid (0.05%) and isopropenyl acetate (0.03%).
U.S. Production · 6 件

2023: 1,000,000 - <2,500,000 lb;2022: 2,500,000 - <4,000,000 lb;2021: 2,500,000 - <4,000,000 lb;2020: 1,000,000 - <2,500,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) GREATER THAN 9.08X10+5 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3821]

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2,4-Pentanedione:;Table: National Aggregate Production Volume (pounds) [Table#3822]

Consumer UsesOther;Solvent;Chemical reaction regulator;Diluent;Corrosion inhibitor
Industry UsesStabilizing agent;Catalyst;Not Known or Reasonably Ascertainable;Diluent;Hardener;Drier;Intermediate;Surface modifier;Laboratory chemicals;Solvent;Dispersing agent;Other;Chemical reaction regulator
Methods of Manufacturing · 3 件

2,4-Pentanedione is produced by thermal or metal-catalyzed rearrangement of isopropenyl acetate (obtained from acetone and ketene). Isopropenyl acetate vapor is fed at atmospheric pressure through a V2A steel tube with an inner temperature of 520 °C. The hot reaction gases are quenched, condensed, and cooled to 20 °C, whereby the gaseous byproducts carbon monoxide, carbon dioxide, methane, and ketene are separated. The product is purified by fractional distillation. Other industrially less important processes for the production of 2,4-pentanedione, include the Claisen ester condensation of ethyl acetate with acetone using sodium ethoxide as condensation agent and the acetylation of acetoacetic acid esters with acetic anhydride in the presence of magnesium salts.

Made by the action of sodium on ethyl acetate and acetone or by the action of anhydrous aluminum chloride on acetyl chloride in the presence of an inert solvent.

Condensation of acetone and acetic anhydride with a boron trifluoride catalyst; reaction of acetone and ethyl acetate in the presence of sodium ethoxide.

応用分野 · 5 件

解説アセチルアセトン,ナトリウムまたはナトリウムアルコキシドの存在下でアセトンと酢酸エチルとをクライゼン縮合させるか,または三フッ化ホウ素の存在下にアセトンと無水酢酸を縮合させることによって得られる.無色の可燃性液体.融点-23 ℃,沸点140 ℃.d254 0.9721.n17D 1.454.希塩酸や有機溶媒に可溶.代表的なβ-ジケトンで,アセト酢酸エチルなどと同様にケト形とエノール形の平衡混合物として存在し,その平衡は溶媒によってかわる(遊離状態では70% がエノール形).多くの金属とキレートをつくるので,各種金属の抽出試薬として使われ,またキレートのなかには接触還元触媒能をもつものが多い.酸化により酢酸を生成し,アルカリ分解するとアセトンと酢酸になる.溶剤,殺虫殺菌剤,そのほか合成中間体など,工業的用途も多い.

用途触媒 (金属キレート) 原料、接着剤原料、溶剤、有機合成中間体 (化学工業日報社)

説明Acetylacetone (2,4-pentanedione) is a clear or slightly yellowish liquid with a putrid odor. It is readily soluble in water and organic solvents, but is incompatible with light, ignition sources, excess heat, oxidizing agents, strong reducing agents, and strong bases. Upon decomposition, acetylacetone releases hazardous products such as carbon monoxide, carbon dioxide, and irritating, toxic fumes. Acetylacetone is used in the production of anticorrosion agents and its peroxide compounds, which serve as radical initiators for polymerization applications. It is also utilized as a chemical intermediate for pharmaceuticals (such as sulfamethazine, nicarbazine, vitamin B6, and vitamin K) and sulfonylurea herbicides. Furthermore, it serves as an indicator for the complexometric titration of Fe(III), for the modification of guanidino and amino groups in proteins, and in the preparation of metal acetylacetonates for catalytic applications.

一般的な説明A colorless or yellow colored liquid. Less dense than water. Flash point 105°F. Vapors are heavier than air. Used as a solvent in paints and varnishes.

使用用途アセチルアセトンは、金属イオンの抽出剤として使用することが可能です。理由として、アセチルアセトンの共役塩基アセチルアセトナート (略号 acac) は、2つの酸素原子を介して二座配位子として多くの遷移金属イオンと六員環結合を形成することが挙げられます。 また、アセチルアセトンの金属錯体には、広範囲にわたる使用用途があります。具体的には、触媒や反応試薬の、NMRシフト試薬、有機合成における遷移金属触媒や、工業的なヒドロホルミル化触媒の前駆体などです。 その他にも、アセチルアセトンは、ガソリンや潤滑油の添加剤としても知られています。近年では、色素増感型太陽電池の開発において、ベースとなる酸化チタン (Ⅳ) にアセチルアセトンを添加すると性能が向上するとの報告があります。

調製方法 · 2 件

2,4-Pentanedione is produced by thermal or metal-catalyzed rearrangement of isopropenyl acetate(obtained from acetone and ketene):Isopropenyl acetate vapor is fed at atmospheric pressure through a V2A steel tube with an inner temperature of 520℃. The hot reaction gases are quenched, condensed, and cooled to 20℃, whereby the gaseous byproducts carbon monoxide, carbon dioxide, methane, and ketene are separated. The product is purified by fractional distillation. Other industrially less important processes for the production of 2,4-pentanedione, include the Claisen ester condensation of ethyl acetate with acetone using sodium ethoxide as condensation agent and the acetylation of acetoacetic acid esters with acetic anhydride in the presence of magnesium salts.

純化方法Small amounts of acetic acid are removed by shaking with small portions of 2M NaOH until the aqueous phase remains faintly alkaline. The sample, after washing with water, is dried with anhydrous Na2SO4, and distilled through a modified Vigreux column (p 11) Cartledge J Am Chem Soc 73 4416 1951]. An additional purification step is fractional crystallisation from the liquid. Alternatively, there is less loss of acetylacetone if it is dissolved in four volumes of *benzene and the solution is shaken three times with an equal volume of distilled water (to extract acetic acid): the *benzene is then removed by distillation at 43-53o and 20-30mm through a helices-packed column. It is then refluxed over P2O5 (10g/L) and fractionally distilled under reduced pressure. The distillate (sp conductivity 4 x 10-8 ohm-1cm-1) is suitable for polarography [Fujinaga & Lee Talanta 24 395 1977]. To recover used acetylacetone, metal ions are stripped from the solution at pH 1 (using 100mL 0.1M H2SO4/L of acetylacetone). The acetylacetone is then washed with (1:10) ammonia solution (100mL/L) and with distilled water (100mL/L, twice), then treated as above. It complexes with Al, Be, Ca, Cd, Ce , Cu, Fe2+, Fe3+ , Mn, Mg, Ni, Pb and Zn. [Beilstein 1 H 777, 1 I 401, 1 II 831, 1 III 3113, 1 IV 3662.]

上流・下流製品情報

下流製品

テトラヒドロジフェルロイルメタン4-メトキシメチル-6-メチル-2-オキソ-1,2-ジヒドロ-3-ピリジンカルボニトリルトリス(2,4-ペンタンジオナト)アルミニウム(III)17-Ethinyl-3,17-dihydroxy-18-methylestra-2,5(10)-diene3-methyletherニンヒドリン3-(3,5-ジメチル-1H-ピラゾール-1-イル)プロパン-1-アミン1,2-DIHYDRO-4-(METHOXYMETHYL)-6-METHYL-5-NITRO-2-OXONICOTINONITRILE4-methoxymethylpyridoxine2-アミノ-4,6-ジメチルピリジン-3-カルボオキサミド5-BROMO-2-CHLORO-4,6-DIMETHYLNICOTINONITRILE4,6-ジメチル-2-(メチルチオ)ピリミジン4,6-DIMETHYL-PYRIMIDINE-2-SULFONYL FLUORIDE

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補足説明

定義ChEBI: A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.

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