2,3-PENTANEDIONE

PRODUCT IDENTIFICATION

CAS NO 600-14-6

2,3-PENTANEDIONE

EINECS NO. 209-984-8
FORMULA CH3COCOC2H5
MOL WT. 100.12

H.S. CODE

2914.19

TOXICITY

Oralrat LD50: 3000 mg/kg
SYNONYMS Pentane-2,3-dione; Acetyl propionyl;
Acetyl propanal; Beta,gamma-dioxopentane;
SMILES

 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE clear to yellow  liquid
MELTING POINT -52 C
BOILING POINT 110 - 112 C
SPECIFIC GRAVITY

0.957

SOLUBILITY IN WATER partially soluble
pH  
VAPOR DENSITY

3.45

REFRACTIVE INDEX

1.404 ± 0.002

NFPA RATINGS

Health: 1; Flammability: 4; Instability: 0

AUTOIGNITION

 

FLASH POINT

18 C

STABILITY Stable under ordinary conditions

GENERAL DESCRIPTION & APPLICATIONS

Diketones are used as a solvent for cellulose acetate, paints, inks, lacquers and as starting materials for the manufacture of target molecules including dyes, pesticides and drugs. 2,3-Pentanedione is used as a constituents of synthetic flavouring agents (Odor description : buttery, cheesy, sweet, nutty, fruity, creamy, caramel). Some examples of aliphatic alpha-diketones found in food additives are:
  • 2-Acetoxy-3-butanone [CAS RN: 4906-24-5]
  • Butan-3-one-2-yl-butanoate [CAS RN: 84642-61-5]
  • Diacetyl [CAS RN: 431-03-8]
  • 2,3-Pentanedione [CAS RN: 600-14-6]
  • 4-Methyl-2,3-pentadione [CAS RN: 7493-58-5]
  • 2,3-Hexadione [CAS RN: 3848-24-6]
  • 3,4-Hexadione [CAS RN: 4437-51-8]
  • 5-Methyl-2,3-hexadione [CAS RN: 13706-86-0]
  • 2,3-Heptanedione [CAS RN: 96-04-8]
  • 2,3-Undecadione [CAS RN: 7493-59-6]
SALES SPECIFICATION

APPEARANCE

clear to yellow  liquid

PURITY (G.C.)

98.0% min

SPECIFIC GRAVITY
0.952 - 0.962
TRANSPORTATION
PACKING
 
HAZARD CLASS 3 (Packing Group: II)
UN NO. 1993
OTHER INFORMATION
Hazard Symbols: F, Risk Phrases: 11, Safety Phrases: 9-16-33
FEMA Number: 2841
GENERAL DESCRIPTION OF DIKETONE
Diketone is a molecule which contains two ketone carbonyl groups. Diacetyl (CH3COCOCH3), 2,3-butadione, is the simplest aliphatic diketone. It is an alpha-diketone which has two ketone groups side-by-side. Usually, alpha-diketone imparts a carmel like or buttery flavor. Diketone compounds take a role in creating various fragrances. Bezil (C6H5COCOC6H5) is an aromatic diketone, the fundamental structure of photo sensitive molecule which is broken down into free radicals upon exposure to ultraviolet radiation. Acetoacetone is a beta-diketone which two ketones are separated only by one carbon. The beta-ketone is stable as a conjugated enol rather than a diketone due to the delocalization which makes the counterion more stable and less likely to regain the proton. Ascorbic acid is an example of enol compound. Enol compounds form complexes with many transition metal ions. These compounds are readily soluble in organic solvents. They are widely used as chelating agents, ligands, and catalyst precursors. Acetoacetic acid and its esters contain active methylene groups which have relatively acidic alpha-protons due to H atom adjacent to two carbonyl groups. The reactivity of its methylene group provide the sequence of reactions of alkylation, hydrolysis of the esters and decarboxylation resulting in substituted ketones. Acetoacetic acid derivatives are important aliphatic parts adjoining azo dyes and pigments. Aacetoacetate is one of Ketone bodies which are the end-products of rapid or excessive fatty acid breakdown in the human body. Para-benzoquinone and its derivatives belong to 1,4-diketone family. Benzoquinone is used as an oxidizing agent in organic chemistry and is a common constituent of biologically molecules like Vitamin K1. Quinones serves as electron acceptors in electron transport chains such as in photosynthesis, and aerobic respiration. Diketene derivatives find versatile applications in making biomolecules, agrochemicals, dyes, pigments, pharmaceuticals including vitamins, and stabilizers for PVC and polyester. They are used as components for fragrances and as solvents. Diketones undergo the reversible and irreversible addition reactions include;
  • Aldol Reactions
  • Alkylation of Enolate Anions
  • Clemmensen Reduction
  • Cyanohydrin Formation
  • Enamine Formation
  • Hemiacetal and Acetal Formation
  • Hydration Formation
  • Imine Formation
  • Wolff-Kishner Reduction